Category: 2199-44-2

Recommanded Product: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Chemistry of pyrrole pigments. III. Nitrogen-hydrogen tautomerism of substituted pyrromethenes. Proton nuclear magnetic resonance spectrometric investigations. Author is Falk, H.; Gergely, S.; Hofer, O..

The temperature-, solvent-, and concentration-dependence of the NMR of the pyrromethenes(I thru VI) was examined and the chem. shifts were assigned and the long range coupling constants were determined Intra- and intermol. proton transfer was observed; tautomeric NH exchanges at -100° were too fast to be measured by NMR.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Iodo derivatives of pyrroles》. Authors are Treibs, Alfred; Kolm, Hans Georg.The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).Computed Properties of C9H13NO2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

Although iodo derivatives of pyrrole are quite stable to alkali, the iodine is rather easily replaced by H, Br, Cl, aryl azo, NO2, and CHR groups. Nitropyrroles are prepared almost exclusively by replacing other substituents by the NO2 group. To 6.7 g. pyrrole and 66 g. KI in 400 cc. 25% EtOH at 30° was added 28 g. AcOH, 10 g. AcONa, 38 cc. 10% H2O2, and 50 cc. H2O; the resulting exothermic reaction was kept 20 min. at 45° giving 2,3,4,5-tetraiodopyrrole, m. 162-4° (decomposition) (EtOH). 2,4-Dimethylpyrrole (I) (3 g.) in 100 cc. MeOH and 9 g. K2CO3 in 100 cc. H2O with 64 cc. M KI3 was shaken until colorless and diluted gradually with H2O to give 9.7 g. 3,5-diiodo derivative (II) of I, m. 83° (aqueous MeOH followed by petr. ether), stable for only 1-2 days. I in EtOH and AcOH with KI3 gave a dark oil yielding only 3-8% II. Formed similarly to II was 2,5-dimethyl-3,4-diiodopyrrole, m. 132°, decompose 135-45° (petr. ether containing Et2O followed by vacuum sublimation), very sensitive to light, especially in solution To 1.75 g. 1,2,5-trimethytpyrrole (III) in 125 cc. MeOH and 10 g. K2CO3 in 50 cc. H2O at -10° was added dropwise 16 cc. M KI3, the mixture kept colorless, filtered promptly from a brown precipitate, and evaporated in vacuo; the residue in petr. ether refiltered and evaporated gave 2.7 g. 3-iodo derivative (IV) of III, m. 71° (MeOH or sublimation), decompose within 30 min. in daylight, stable 1-2 days under extreme precautions. III (1 g.) and 10 g. K2CO3 in 180 cc. 60% MeOH treated in 1 portion with 4.6 g. iodine in 50 cc. MeOH gave 3.2 g. 4-iodo derivative of IV, pale yellow, m. 129° (dilute EtOH). Formed similarly to IV from 2,3,4-trimethylpyrrole (V) (using iodine in MeOH), was the 5-iodo derivative of V, m. 90° (petr. ether at -70°), giving a pos. Ehrlich reaction at 20°, decomposing readily in warm solution From 3-formyl derivative of I in alk. MeOH was formed 90.4% 3-formyl-5-iodo derivative of I, m. 157° (MeOH), also prepared in similar yield by treating 2.5 g. 3-formyl derivative of I in 20 cc. EtOH with 3 g. AcONa and 2.3 g. H2O2, acidifying with 2 g. AcOH at 40-50°, and adding 2.3 g. KI in H2O. By either of these methods, the 5-formyl derivative of I gave 84-6% 3-iodo-5-formyl derivative of I, m. 172° (EtOH). In alk. MeOH containing KI3 and in AcOHMeOH with KI and 3% H2O2 2-methyl-3-carbethoxypyrrole (VI) gave 90-94% 4,5-diiodo derivative of VI, pale pink, m. 191° (decomposition) (when rapidly heated). From 2 g. 3-methyl-2,4-dicarbethoxypyrrole (VII) in 30 cc. 50% EtOH at 80° with 8.9 cc. M KI3 (gradually added) was formed 2.8 g. 5-iodo derivative (VIII) of VII, m. 174° (EtOH), also prepared by Kleinspehn and Corwin’s method (C.A. 49, 285g); under these conditions a hitherto undescribed very insoluble dark green iodine adduct of VIII (not analyzed) was also formed. The 5-carbethoxy derivative of I in acid solution by the usual procedures gave 98% 3-iodo-5-carbethoxy derivative (IX) of I, nacreous leaflets, m. 141°, also formed from the 3-carboxy analog of IX by iodination and decarboxylation. IX heated with alk. MeOH gave the 5-CO2Me analog of IX, m. 182°. Formed by the usual procedures from the 3-carbethoxy derivative of I or its 5-carboxy derivative was the 3-carbethoxy-5-iodo derivative (IXa) of I, m. 146°. IX stirred with KOH at 135-40° and acidified with HCl gave 3-iodo-5-carboxy derivative of I, m. 112° (decomposition), giving a pos. Ehrlich reaction; this could not be converted into the 3-iodo derivative of I by thermal decarboxylation. To 3.94 g. of the product formed by condensing VI with BzH (Fischer and Schubert, C.A. 21, 381) in 50 cc. MeOH and 3 g. K2CO3 in 10 cc. H2O was added gradually 20 cc. M KI3 and the mixture boiled briefly giving (HN.CHMe:CR.CI:C)2CHR’ (X) (R = CO2Et, R’ = Ph), m. 217-18° (decomposition) (when rapidly heated). Formed analogously was X (R = CO2Et, R’ = Me), m. 168° (decomposition) (MeOH). In either case X was identified by coupling with p-O2NC6H4N2OAc and subsequent fission giving p-O2C6H4N:NC:CI.CR:CHMe.NH (Xa) (R = CO2Et) (cf. C.A. 52, 13705g). The 4,5-diiodo derivative of VI refluxed with 0.5 g. NH4Cl and 15 cc. 80% EtOH with gradual addition of 0.3 g. Zn dust, filtered, and treated with 75 cc. H2O containing little NH4OH or HCl gave VI, m. 72°. This method failed to remove iodine from the 5-iodo derivative of VII, which however with Zn in warm glacial AcOH gave VII, m. 91°. Under similar conditions the 5-Br derivative of VII remained unchanged. The 4-iodo-5-nitro derivative (Xb) of VI (0.65 g.) refluxed 30 min. with 0.32 g. Natur-kupfer C and 15 cc. glacial AcOH, filtered hot, and treated with 10% HCl gave 90% 5-NO2 derivative of VI, m. 144°, giving deep yellow alk. solutions, yielding pale yellow needles on acidification, giving no Ehrlich reaction and extremely unreactive. The following could be reduced similarly by means of the same catalyst: IX, the 5-iodo derivative of VII, and the 4,5-iodo derivative of VI. None of the corresponding Br derivatives was affected by this catalyst. IX (0.3 g.) in 5 cc. Ac2O warmed gently with 0.8 g. KI did not react until small amounts of H2O were added to the hot solution followed by cold H2O, whereupon a mixture of IX and the 5-CO2Et derivative of I was formed. On long standing the amounts of IX increased, but in the presence of NaHSO3 the yield of 5-CO2Et derivative of I was quant. In the above reaction KBr could replace KI, but KCl or NH4Cl were inactive unless IX was prehydrolyzed with HCl. The 3-iodo-5-carboxy derivative of I warmed with dilute HCl, made alk. with NaOH, and extracted with Et2O gave I (picrate, m. 90°). IX in 10 cc. 70% Et2O treated with BF3, poured on ice, and neutralized with Na2CO3 gave mostly black products and little I. In the presence of Cu, BF3-Et2O reacted with IX at 50° giving 5-CO2Et derivative of I, m. 122°. IXa with equimolar amounts of Ph3P in dry Et2O after 2 hrs. gave unanalyzed yellow crystals (XI), m. 218° (N-free), the filtrate from which gave the 3-CO2Et derivative of I, m. 75°. IX gave a similar reaction with Ph3P but required 2 weeks to give XI; the filtrate gave the 5-CO2Et derivative of I. In 100-200 mg. of various iodo- and bromopyrroles, the % halogen could be determined by treating with equal amounts of KI in 50-80 cc. 80% MeOH at 50-60°, acidifying with 2N H2SO4, and titrating with 0.1N Na2S2O3. Usually the results were satisfactory. However the iodo derivatives of VII and X reacted so slowly with hot methanolic KI solutions that the method could not be used. A technique for the qual. identification of iodine in pyrrole derivatives is described. To 0.5 g. 3,5-di-CO2Et derivative of I in 30 cc. MeOH at 0° 1 g. iodine in MeOH was added gradually and the mixture poured into 400 cc. ice-cold 1% aqueous KI giving the deep blue adduct C12H17NO4.I, m. 146° (after washing with H2O and drying rapidly over P2O5), which in hot EtOH gave the original pyrrole, m. 137°. Similarly, the 5-Bt derivative of VII gave the adduct C11H14BrNO4.I, m. 152-4°, decolorized at 60° by aqueous alcoholic KI, but giving the adduct on cooling. Similar (undescribed) iodine adducts were obtained with pyrrole, VII, and the 5-CO2H derivative of VII; the latter on heating in alk. solution gave VIII. IX (4 g.) was added gradually to 30 cc. concentrated HNO3 at 0°, kept 1 hr., the precipitate washed with H2O and triturated with little aqueous NaHCO3, and extracted with 2 g. KI; the residue gave 2.5 g. 3-nitro-5-carbethoxy derivative (XII) of I, m. 204° (CHCl3); the corresponding 5-CO2Me analog, m. 184°. XII (65%) was also formed by adding the 5-CO2Et derivative of I at 0° to HNO3 and after 10 hrs. pouring into ice H2O. From IXa and HNO3 at -10° was formed 55% 3-carbethoxy-5-nitro derivative of I, m. 149° (dilute EtOH), identical with the compound obtained by Fischer and Zerweck (C.A. 17, 106). From the 4,5-diiodo derivative of VI and HNO3 was formed 75% Xb, m. 181°, and from VIII was formed the 5-NO2 derivative of VII, pale yellow, m. 111° (ligroine). The 4,5-diiodo derivative of VI (0.5 g.) in 30 cc. glacial AcOH with 0.24 g. p-O2NC6H4N2OAc in 5 cc. AcOH gave Xa, orange red, m. 186-7° (decomposition) (EtOH), soluble in MeOH containing NaOH, reprecipitated with acid. Similarly the 4-iodo derivative of IV gave 1,2,5-trimethyl-3-iodo-4-(p-nitrophenylazo)pyrrole, brown needles, sintering 160°, m. 185° (decomposition), 2,3,4,5-Tetraiodopyrrole similarly gave 2,3,4-triiodo-5-(p-nitrophenylazo)pyrrole, red, m. 221° (decomposition), giving a violet solution in alk. MeOH, reprecipitated by HCl. No azo dye was isolated by similar treatment of the 3-formyl-5-iodo and 5-formyl-3-iodo derivatives of I, X, or the 5-NO2 derivative of VI. IXa (2.9 g.) in 25 cc. EtOH was boiled briefly with 0.5 cc. 30% HCHO and 1 cc. concentrated HCl added dropwise giving bis(2,4-dimethyl-3-carbethoxy-5-pyrryl)methene-HCl, red with blue surface luster, m. 224° (cf. Fischer and Zerweck, C.A. 17, 1465), which in boiling EtOH with NH4OH gave the corresponding free methene (XIII), yellow, m. 190°. IXa treated as above, but in cold MeOH, with HCHO and a drop of 2N HCl and after 15 hrs. made barely alk. with 2N NaOH and crystallized from MeOH gave a mixture which was fractionated from CHCl3 giving 18% less soluble bis(2,4-dimethyl-3-carbethoxy-5-pyrryl)methane (XIIIa), m. 224°, whose mother liquor gave 73% XIII. IXa (2.9 g.) in 25 cc. hot EtOH with 0.5 cc. 30% HCHO was heated with 5 g. Na2S2O3 in 15 cc. H2O and acidified with HCl to pH 3. The precipitate was triturated with hot EtOH containing little NaOH and filtered giving XIIIa and from the mother liquor bis(2,4-dimethyl-3-carbethoxy-5-pyrryl) sulfide, C18H24N2O4S, m. 198-200° (slowly heated), 212° (rapid heating) (CHCl3-petr. ether followed by CCl4). IXa in EtOH with BzH and little HCl refluxed 30 min. and made alk. with dilute NH4OH gave 30% ms-phenylbis(2,4-dimethyl-3-carbethoxy-5-pyrryl)methene (XIV), orange-red, m. 158° (MeOH); HCl salt, m. 204°. Very similarly, IXa and 1,4-C6H4(CHO)2 in EtOH with a trace of concentrated HCl refluxed 10 min. gave a dark crystalline deposit which was triturated with 20% EtOH and warm H2O and treated with NH4OH giving p-phenylenebis [ms-bis(2,4-dimethyl-3-carbethoxy-5-pyrryl)methene], pale orange, turning black at 272° (CHCl3 and xylene), turning dark red on exposure to direct sunlight, which when treated with Zn and HCl in EtOH at 40° gave a colorless compound, m. 267° (putatively the corresponding methane, but not analyzed). By the usual procedure, IXa and p-Me2NC6H4CHO yielded ms-(p-dimethylaminophenyl)bis(2,4-dimethyl-3-carbethoxy-5-pyrryl)-methen-HCl, coarse dark crystals, m. 224-5° (even when the alcoholic solution was made alk. with NH4OH), which in 80% MeOH containing a little HCl treated with an excess 2N NaOH and heated gave the free methene, C27H33N3O4, red rodlets with green luster, m. 183°. XIIIa (70 mg.) in 20 cc. MeOH treated gradually with 68 mg. ICl in 2 cc. MeOH gave XIII. XIV was similarly formed from the corresponding methane. Tetrakis(2,4-dimethyl-3-carbethoxy-5-pyrryl)ethane and tris(2,4-dimethyl-3-carbethoxy-5-pyrryl)methane oxidized with ICl both gave XIII. IX (3 g.) in 20 cc. AcOH was boiled 20 min., treated with a mild stream of air, and distilled; any loss of AcOH was compensated for by AcOH addition H2O added to the distillate gave a dark precipitate which treated with C and fractionated from dilute EtOH gave principally the 5-CO2Et derivative of I, m. 122°, very small amounts of 3-Ac-5-CO2Et derivative of I, m. 142°, and after high vacuum sublimation at 120° [MeC:C(CO2Et).NH.CMe:C]2 (XV), m. 186°, showing a pale yellow-green fluorescence in EtOH, colorless in ligroine, giving no Ehrlich test, and forming no azo dye with p-O2NC6H4N2OAc in acid unless previously heated with alk. MeOH, after which both reactions were pos. An attempt to form a bipyrrole derivative analogous to XV by the deiodination of IXa gave an orangered compound, m. 254° (ligroine, CCl4, or CHCl3-Et2O), containing about 63% C, 6.6 H, and 8.0 N; the mother liquor gave 3-CO2Et derivative (XVI) of II, m. 76°. IXa in glacial AcOH with N Br in AcOH with addition of dilute Na2S2O3 gave the corresponding 5-Br analog (XVII) of IXa, m. 96° (decomposition) (when rapidly heated), m. 102° (decomposition), also formed by treating IXa in AcOH with concentrated aqueous HBr and crystallizing from dilute AcOH. When in this reaction excess Na2SO3 was added, XVI was obtained. IXa (200 mg.) in 4 cc. AcOH, 0.5 cc. concentrated HCl, a little H2O, and small amounts of Br followed by (but avoiding an excess of) Na2S2O3 gave the 5-Cl analog of IXa, m. 140° (decomposition) (aqueous MeOH or dilute AcOH), also formed from XVII. The 5-CO2Et derivative of I in AcOH with excess concentrated HCl and equivalent amounts of Br gave 5-CO2Et-3-Cl derivative of I, m. 182-3° (EtOH); 32 references.

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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Derivatives of pyrrylazobenzenearsonic acids》. Authors are Muic, N.; Fles, D..The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).Recommanded Product: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

cf. C.A. 45, 9526a. The synthesis is essentially the same as previously described. 2,4-Dimethyl-3,5-carbethoxypyrrole (I) was prepared by the method of Knorr. I was saponified in 10% KOEt, and converted to 2,4-dimethyl-3-carbethoxy-5-pyrrolecarboxylic acid (II) by the method of Küster, et al. (C.A. 16, 3895). Decarboxylation of II by dry distillation gave 2,4-dimethyl-3-carbethoxypyrrole (III). I was also treated with concentrated H2SO4 by the method of Fischer and Walach (C.A. 20, 1620) to give 2,4-dimethyl-5-carbethoxy-3-pyrrolecarboxylic acid, which was decarboxylated by heating at atm. pressure to 2,4-dimethyl-5-carbethoxypyrrole (IV). Attempts to couple diazotized 4, 3-H2N(O2N)C6H3AsO3H2 and III were not successful; a resinous product, which could not be purified, was obtained, and III was isolated from the reaction mixture Attempts to couple a salt of diazotized 3,4-H2N(HO)C6H3AsO3H2 (V) with IV were also unsuccessful. p-H2NC6H4AsO3H2 (4.34 g.) in 50 cc. H2O containing 1.63 cc. concentrated H2SO4 was diazotized with 20 cc. N NaNO2 at 0-5° and the product filtered into 3.34 g. III in 200 cc. absolute EtOH. 4-(3-Carbethoxy-2,4-dimethyl-5-pyrrylazo)benzenearsonic acid (VI) precipitated as an orange-yellow powder. VI was filtered, rinsed with water, dissolved in aqueous NaOH, and the solution clarified with active C; acidification with dilute HCl gave 4.3 g. VI, orange-yellow microcrystals, decompose 210°, slightly soluble in water, somewhat more soluble in EtOH, nearly insoluble in C6H6 and ether, and soluble in dioxane; crystallization from dioxane gave well-formed needles. VI was precipitated from alk. solution with dilute acids. VI was stable in air under light. V (4.66 g.) in 70 cc. H2O containing 5.8 cc. concentrated H2SO4 was diazotized as above and the product filtered into 3.34 g. III in 200 cc. absolute EtOH. 2-(3-Carbethoxy-2,4-dimethyl-5-pyrrylazo)-1-phenol-4-arsonic acid (VII) precipitated, and addnl. amounts of VII were obtained on diluting with H2O. VII was then dissolved in N NaOH, the solution clarified with active C, added to 0.1 N HCl with constant stirring, and the precipitate was filtered, washed with H2O, dried, and recrystallized twice from dioxane to yield 7.2 g. VII, yellow needles, decompose 160°. VII was stable in air under light. (p-H2NC6H4)2As(:O)OH (1.46 g.) in 30 cc. H2O containing 3.7 cc. concentrated HCl was diazotized as above with 10 cc. N NaNO2 and the solution added dropwise at 5° or lower to 1.67 g. III in 70 cc. EtOH containing 5 g. NaOAc, previously dissolved in a small volume of H2O, to yield di-Et 5, 5′-[arsinobis(p-phenyleneazo)]bis[2,4-dimethyl-3-pyrrolecarboxylate] (VIII). VIII was filtered, washed with cold H2O, dried in vacuo, and recrystallized from dioxane and then from ether to yield 1 g. VIII, dark orange microcrystals, m. 151° (decomposition). VIII was soluble in EtOH, dioxane, and CHCl3. p-H2NC6H4AsO3H2 (2.17 g.) in 25 cc. H2O containing 0.81 cc. concentrated H2SO4 was diazotized with 10 cc. N NaNO2 and the product filtered into 1.67 g. IV in 200 cc. absolute EtOH; when the solution was clear 15 g. NaOAc in a small amount of H2O was added with cooling, and, after 1 hr., 4 l. H2O was added to precipitate 4-(5-carbethoxy-2,4-dimethyl-3-pyrrylazo)benzenearsonic acid (IX), yellow-orange powder. IX was twice dissolved in alkali and reprecipitated by dilute HCl, washed with water, and dried in vacuo to yield 1.2 g. IX, darkens 100°, m. 185° (decomposition), IX was soluble in EtOH and dioxane, and stable in air under light.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Improved synthesis of covalently strapped porphyrins. Application to highly deformed porphyrin synthesis, published in 1988-04-01, which mentions a compound: 2199-44-2, mainly applied to porphyrin strapped; polymethyleneporphyrin, Quality Control of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

The title porphyrins I (n = 1, 2, 3) were prepared α,ω-Dicarboxyalkyl dichloride, was treated with 2 equiv of 2-(ethoxycarbonyl)-3,5-dimethylpyrrole, and the chain-linked bis[5-(ethoxycarbonyl)pyrrole] so obtained was transformed into the pyrrole-2-carboxaldehyde by using standard methodol. Protection of the formyl groups as the dicyanovinyl derivative and the activation of the 2-Me substituents with SO2Cl2 gave the bis[2-(chloromethyl)pyrrol)], which on reaction with a 5-unsubstituted 2-pyrrolecarboxylate, in warm AcOH, afforded the chain-linked dipyrromethane dimer in high yield. Regeneration of the formyl substituents and removal of the ester group produced the 5-formyldipyrromethane dimer II, which was cyclized intramolecularly, under high dilution, to give I. II (n = 0) failed to cyclize.

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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Double-helical dinuclear bis(dipyrromethene) complexes Formed by self-assembly, published in 2000-11-17, which mentions a compound: 2199-44-2, mainly applied to transition metal dipyrromethene complex preparation; pyrromethene transition metal complex preparation; crystal structure transition metal dipyrromethene complex; helix double transition metal dipyrromethene complex preparation, Formula: C9H13NO2.

Bis(dipyrromethene) ligands linked by an alkyl spacer between β and β’ positions (I; n = 1, 2, 3) give helical dimers or monomers, dependent upon the length of the alkyl linker, upon complexation. Ligands consisting of methylene, ethylene, and propylene linkers -(CH2)n- (n = 1, 2, and 3) give helical dimers, while longer linking chains (n = 4, 5, or 6) give monomers or mixtures of dimers and monomers. X-ray crystal structures of the dimeric Zn complexes (n = 1, 2, and 3) reveal that the angles between dipyrromethene planes and the extent of helicity in the complexes differ as the length of the linker varies. The extent of helicity was assessed and is dependent upon the length and, specifically, the conformational preferences of the alkyl spacer unit. The presence of an ethylene linker gave complexes of greatest helicity. The use of a methylene spacer gave less helical structures upon complexation, while propylene spacers gave only slightly helical complexes. These studies identify the crucial importance that the conformational preferences of the β-β’ alkyl spacer group plays in the coordination algorithm of self-assembly to form dipyrromethene based complexes.

Here is just a brief introduction to this compound(2199-44-2)Formula: C9H13NO2, more information about the compound(Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate) is in the article, you can click the link below.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《A novel route to certain 2-pyrrolecarboxylic esters and nitriles》. Authors are Kleinspehn, Geo. G..The article about the compound:Ethyl 3,5-Dimethyl-2-pyrrolecarboxylatecas:2199-44-2,SMILESS:O=C(C1=C(C)C=C(C)N1)OCC).Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

HON:C(CO2Et)2 (I) underwent reduction and condensation with certain β-diketones and a β-oxo aldehyde to give 2-pyrrolecarboxylic esters. Similarly, HON:C(CN)CO2Et (II) and certain β-diketones afforded 2-pyrrolecarbonitriles. The method has been applied to the synthesis of 5 previously known pyrroles. This synthetic approach constitutes the most direct route to 4 of these 5 pyrroles. A sixth and previously unreported pyrrole, 3,5-dimethyl-2-pyrrolecarbonitrile (III), also has been prepared by this method. Ac2CH2 (5.00 g.) in 26 cc. glacial AcOH heated with vigorous stirring at 80° with 13 g. NaOAc and 11 g. Zn dust, the mixture then treated with 9.47 g. I in 12 cc. AcOH and 5 cc. H2O dropwise at 95-105° during 30-40 min., heated 20 min. at 100-5°, poured with stirring into 170 cc. ice water, and refrigerated, the precipitate washed with H2O, pressed dry, dissolved in 50 cc. boiling EtOH, and filtered hot, the filtrate concentrated to 30 cc., poured into 85 cc. ice water, and refrigerated, and the crystalline deposit dried in vacuo (5.03 g.), and recrystallized twice from 95% EtOH yielded 2-carbethoxy-3,5-dimethylpyrrole (IV), m. 124-4.5°. I and Ac2CHEt (50 millimole each), b23-3.5 79-83.5°, gave by the same procedure 6.36 g. 4-Et derivative of IV, m. 90-1° (from 95% EtOH). I and Ac2CH(CH2)2CO2H (50 millimoles) treated in the same manner, the reaction mixture treated with 5 cc. concentrated HCl, and the crude product (7.08 g.) recrystallized from boiling C6H6 gave 5-carbethoxy-2,4-dimethyl-3-pyrrolepropionic acid, m. 154-6°. NaOAc (7.9 g.) added with stirring to 29 cc. glacial AcOH at 85°, the mixture treated with 7.00 g. AcCHMeCHO, 9.48 g. I, and 12 cc. glacial AcOH in 5 cc. H2O, followed by 11 g. Zn dust at 95-105°, stirred 20 min., poured into 170 cc. ice water, and refrigerated, and the deposit dissolved in 10 cc. boiling EtOH and filtered, the filtrate poured into 20 cc. ice water, and the precipitate (2.49 g.) recrystallized from 95% EtOH and then twice from isoöctane gave 2-carbethoxy-3,4-dimethylpyrrole (V), m. 75-6.5°. V heated briefly in EtOH with excess 40% aqueous CH2O and a few drops concentrated HCl yielded 5,5′-methylenebis(2-carbethoxy-3,4-dimethylpyrrole), m. 202-3°. II and Ac2CH2 (50 millimoles each) treated by the usual procedure, the crude product containing the Zn dust dissolved in 25 cc. boiling 95% EtOH, and the filtrate poured into 75 cc. ice water yielded 2.48 g. IV, m. 24-5° (recrystallized from EtOH and sublimed). Glacial AcOH (26 cc.) and 5.00 g. Ac2CH2 heated to 80°, the mixture treated consecutively with 13 g. NaOAc, 7.11 g. II, and 12 cc. AcOH in 5 cc. H2O, heated to 95°, treated during 20-5 min. with 11 g. Zn dust at 95-105°, stirred 20 min., and poured into ice water, the precipitate refrigerated, filtered off, dissolved in 15 cc. boiling EtOH, and filtered, the filtrate stirred into 30 cc. ice water and refrigerated, and the crude precipitate (2.10 g.) recrystallized twice from isoöctane yielded III, m. 75-6.5°. II and Ac2CHEt gave similarly 45% crude 4-Et derivative of III, m. 135-6°.

Here is just a brief introduction to this compound(2199-44-2)Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, more information about the compound(Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate) is in the article, you can click the link below.

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Application In Synthesis of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Synthesis of a series of substituted 2-ethoxycarbonylpyrroles. Author is Yu, Xiang-hao; Yang, Nian-fa; Cao, Jing.

The synthesis of 2-(ethoxycarbonyl)-3,4-dimethylpyrrole (I) was studied. A series of substituted 2-(ethoxycarbonyl)pyrrole was prepared by reaction of oxo olefin salt with di-Et aminomalonate. For example, refluxing MeCOCMe:CHONa with di-Et aminomalonate in aqueous HOAc for 2 h gave 35% I.

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The preparation of ester heterocycles mostly uses heteroatoms as nucleophilic sites, which are achieved by intramolecular substitution or addition reactions. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ) is researched.HPLC of Formula: 2199-44-2.Vom, Amelia; Headey, Stephen; Wang, Geqing; Capuano, Ben; Yuriev, Elizabeth; Scanlon, Martin J.; Simpson, Jamie S. published the article 《Detection and Prevention of Aggregation-based False Positives in STD-NMR-based Fragment Screening》 about this compound( cas:2199-44-2 ) in Australian Journal of Chemistry. Keywords: fragment screening saturation transfer difference NMR ketopantoate reductase. Let’s learn more about this compound (cas:2199-44-2).

Aggregation of small organic compounds is a problem encountered in a variety of assay screening formats where it often results in detection of false positives. A saturation transfer difference-NMR-detected screen of a com. available fragment library, followed by biochem. assay, identified several inhibitors of the enzyme ketopantoate reductase. These inhibitors were subsequently revealed to be aggregation-based false positives. Modification of the fragment screen by addition of detergent in the saturation transfer difference-NMR experiments allowed an assay format to be developed that resulted in the identification of genuine hit mols. suitable for further development.

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Most of the compounds have physiologically active properties, and their biological properties are often attributed to the heteroatoms contained in their molecules, and most of these heteroatoms also appear in cyclic structures. A Journal, Khimiya Geterotsiklicheskikh Soedinenii called Synthesis and some reactions of pyrroles with aliphatic acyl substituents, Author is Mironov, A. F.; Ol’shanskaya, N. B.; Zhestkov, V. P.; Evstigneeva, R. P., which mentions a compound: 2199-44-2, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2, Synthetic Route of C9H13NO2.

4-Acylpyrrolecarboxylates (I; R = EtCO, C15H31CO, C17H35CO) were prepared in about quant. yields of Friedel-Crafts acylation of I (R = H). Reduction of I by NaBH4 gave 82-97% of alc. (II; R = Et, C15H31, R1 = H). Heating II (R = C15H31, R1 = H) in pyridine with Ac2O gave 96% acryl derivative II (R = C15H31, R1 = Ac). Treatment of I (R = C17H35CO) with Pb(OAc)4 gave an acylated intermediate which with 40% HBr and MeOH gave 85% pyrrole (III; R = C17H35CO, R1 = MeO). Similarly III (R = C15H31CO, R1 = Cl) was obtained in 75% yield.

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Related Products of 2199-44-2. The protonation of heteroatoms in aromatic heterocycles can be divided into two categories: lone pairs of electrons are in the aromatic ring conjugated system; and lone pairs of electrons do not participate. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Synthesis and spectral properties of 3,3′-bis(dipyrrolylmethene). Author is Dudina, N. A.; Berezin, M. B.; Guseva, G. B.; Semeikin, A. S..

Bis(2,4,7,8,9-pentamethyldipyrrolylmethen-3-yl)(4′-methoxyphenyl)methane dihydrobromide was synthesized and its spectral properties were studied. The basicity of the ligand 3,3′-bis-(dipyrrolylmethene) decreases upon insertion of the methoxyphenyl group in the 3,3′-spacer.

Here is just a brief introduction to this compound(2199-44-2)Related Products of 2199-44-2, more information about the compound(Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate) is in the article, you can click the link below.

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