Category: 2199-44-2

The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Some transformations of 2,4-dimethylpyrrole》. Authors are Fischer, Hans; Weiss, Bernhard; Schubert, Max.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).Formula: C9H13NO2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

From 0.9 g. 2,4-dimethylpyrrole (I) and 0.8 g. MeCN in cold Et2O saturated with dry HCl and allowed to stand 1 day is obtained 0.7 g. of the ketimine, m. 100°, sublimes 100° (HCl salt, green needles), of 2,4-dimethyl-5-acetylpyrrole (II). The ketimine is reduced by H and Pt sponge in alc. to I and when boiled with H2O to disappearance of the NH3 odor, 0.7 g. of it gives 0.3 g. II, m. 121°. 2,4-Dimethyl-5-chloroacetylpyrrole (0.9 g. from 1 g. I and 1 g. MeCN in cold Et2O saturated with dry HCl and allowed to stand 0.5 hr. in ice), m. 143°, gives in alc. with 30% NHMe2 after 0.5 hr. at 100° the 5-dimethylaminoacetyl derivative, m. 110°, while 0.5 g. boiled 0.5 min. in alc. with 40% HCHO and a few drops concentrated HCl yields 0.4 g. bis-[2,4-dimethyl-5-chloroacetylpyrryl]methane, m. 258°, which with NHMe2 in alc. gives the bis-5-dimethylaminoacetyl derivative m. 170°. I (1 g.) boiled up several times with 2 g. of 90% HCO2H and 10 drops of 20% HClO4 and allowed to stand 1 day gives 0.5 g. of the perchlorate, becomes discolored 200°, does not m. 260°, of bis-[2,4-dimethyl-pyrryl]methene, yellow, m. 117°. 2,4-Dimethyl-5-carbethoxypyrrole (III), obtained in 60-70% yield from I and EtMgBr and subsequent treatment with ClCO2Et, m. 125°, gives a positive Ehrlich aldehyde reaction in the cold, is hydrolyzed by boiling 50% KOH to the free acid, m. 136°, also obtained from the above Grignard compound with CO2. 2,4-Dimethyl-5-carbethoxypyrrole-3-aldehyde (IV). obtained in 85% yield from III and HCN in cold Et2O saturated with dry HCl and subsequent decomposition of the resulting imide chloride with hot H2O, m. 145°, gives a faint Ehrlich aldehyde reaction in the cold, more strongly on heating; 3 g. heated with 1:1 KOH until completely dissolved (about 15 min.) gives 2.2 g. of the free 5-carboxyaldehyde, m. 230°, which on distillation in vacuo yields 2,4-dimethylpyrrole-3-aldehyde, m. 126°, gives a positive aldehyde reaction even in the cold. Phenylhydrazone of IV, m. 204°. Azlactone, C19H18O4N2 (1.3 g. from 1.2 g. IV, 1.8 g. hippuric acid, 2.2 g. NaOAc and 20 cc. Ac2O heated 35 min. on the H2O bath), m. 232°. Oxime, m. 196-7°, converted by boiling NaOAc-Ac2O into the nitrile, C10H12O2N2, m. 171°. Semicarbazone, m. 285° (decomposition), converted by Na in alc. after 8 hrs. at 160-70° into 2,3,4-trimethylpyrrole. 2,4-Dimethyl-5-carbethoxy-3-chloroacetylpyrrole, from III and ClCH2CN, m. 163°, gives a faint positive Ehrlich reaction on heating, is highly sternutatory when powdered, gives in boiling alc. with aqueous KCN the 3-cyanoacetyl derivative, m. 172-3°.

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.

Reference:
Thiazolidine – Wikipedia,
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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Molecular compounds of pyrroles》. Authors are Dezelic, Mladen.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).Formula: C9H13NO2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

The following data were obtained by means of f.-p. determinations In each case the eutectic point is given in mole % of the 2nd component; T. P. = transition point. 2,4-Dimethyl-3-acetyl-5-carbethoxypyrrole (I): AcOH, no solid compound; succinic acid (II), 25%, 126.5°; BzCH (III), 63% 87.5°; ClCH2CO2H (IV), 91%, 52° (T. P., 55%, 85.3°); PhOH (V), 90%, 27° (T. P. 55%, 93°), salicylic acid (VI), 58%, 106° (2 T. P., 38%, 113°, and 50%, 107°); therefore 2 compounds 2I.VI and I.VI; picric acid (VII), 60%, 94° (T. P., 50%, 97.8°); o-C6H4(OH)2 (VIII), 57%, 71° (T. P., 41%, 108.5°); m-C6H4(OH)2 (IX), 2 eutectics, 19%, 132.5°, and 78%, 44° (maximum at 33.3% and 139°); p-C6H4-(OH)2 (X), 2 eutectics, 10%, 138.2° and 62%, 135° (maximum at 33.3%, 153°). 2,4-Dimethyl-5-carbethoxypyrrole (XI): IV, 80%, 49°; V, 86%, 23°; VI, 40%, 94.5°; VIII, 66%, 71°; IX, 56.5%, 74.5°; X, 32%, 106°; VII, 66%, 94° (T. P., 33.3%, 100°; compound, 2XI.VII). 2,4-Dimethyl-5-carbethoxypyrrole-3-aldehyde (XII): IV, 86%, 51° (T. P., 60%, 74.5°; compound, XII.IV); III, maximum at 50% and 135°, 2 eutectics; VII, 60%, 95.5° (T. P., 50%, 97°); VIII forms the compound XII.VIII, m. 114° (2 eutectics); X forms the compound 2XII.X, m. 142° (2 eutectics). 2,5-Dimethyl-3-carbethoxypyrrole-4-aldehyde (XIII):VIII, 67%, 56°; IX, 61%, 80°, compound XIII.IX, m. 98°; compound XIII.X, m. 117.5°; VI forms 2 compounds, 2XIII.VI, and XIII.VI, eutectics 42%, 109° and 57.5%, 109° (T. P., 36%, 111°).

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Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Selective β-chlorination of 1-benzoyl-2-ethoxycarbonyl-3,5-dimethylpyrrole with iodobenzene dichloride. Preparation of ethyl 4-chloro-3,5-dimethylpyrrole-2-carboxylate. Author is Angelini, Giancarlo; Sleiter, Giancarlo.

Chlorination of I (R = H, R1 = Bz) with PhI+ClCl- in CHCl3 at -15° in the dark, followed by debenzoylation of the product gave I (R = Cl, R1 = H). Reaction of I ( R = R1 = H) with Cl, SO2Cl2, or PhI+ClCl- in CHCl3 or ether at low temperature resulted in simultaneous chlorination of both the β-position and the α-methyl group.

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Application In Synthesis of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Aromatic heterocyclic compounds can also be classified according to the number of heteroatoms contained in the heterocycle: single heteroatom, two heteroatoms, three heteroatoms and four heteroatoms. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Carbon-13 nuclear magnetic resonance spectra of substituted pyrroles. Author is Abraham, Raymond J.; Lapper, Roy D.; Smith, Kevin M.; Unsworth, John F..

The 13C NMR spectra of 55 pyrroles were determined and assigned. The pyrrole ring carbon chem. shifts were predicted, to ∼0.5 ppm, on the basis of additive substituent effects and contributions from steric and conjugative effects. The substituent chem. shift parameters were analogous to those for thiophenes. C-2 substituents affected mainly C-3 and C-5, and C-3 substituents mainly C-2.

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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 Characterization, chemical optimization and anti-tumor activity of a tubulin poison identified by a p53-based phenotypic screen, published in 2008-11-01, which mentions a compound: 2199-44-2, mainly applied to JJ781 derivative antitumor design preparation structure activity p53 tubulin, SDS of cas: 2199-44-2.

A robust p53 cell-based assay that exploits p53’s function as a transcription factor was used to screen a small mol. library and identify bioactive small mols. with potential antitumor activity. Unexpectedly, the majority of the highest ranking hit compounds from this screen arrest cells in mitosis and most of them impair polymerization of tubulin in cells and in vitro. One of these novel compounds, JJ78:1, was subjected to structure-activity relationship studies and optimized leading to the identification of JJ78:12. This mol. is significantly more potent than the original hit JJ78:1, as it is active in cells at two-digit nanomolar concentrations and shows clear antitumor activity in a mouse xenograft model as a single agent. The effects of nocodazole, a well established tubulin poison, and JJ78:12 on p53 levels are remarkably similar, supporting that tubulin depolymerization is the main mechanism by which JJ78:12 treatment leads to p53 activation in cells. In summary, these results identify JJ78:12 as a potential cancer therapeutic, demonstrate that screening for activators of p53 in a cell-based assay is an effective way to identify inhibitors of mitosis progression and highlights p53’s sensitivity to alterations during mitosis.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Alcoholytic, phenolytic and hydrolytic cleavage of organic compounds by catalysts. II》. Authors are Houben, J.; Fischer, Walter.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).Formula: C9H13NO2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

cf. C. A. 25, 3311. As shown recently, trihalomethyl ketones are not only converted stoichiometrically into alkali carboxylates and CHCl3 by aqueous alkali (Reaction 1) but also undergo another, purely catalytic reaction; even in the cold they react with alcs. according to the equation RCOCCl3 + R’OH = RCO2R’ + CHCl3 (Reaction 2). It was thought that an alcoholate was indispensable as the catalyst and that water must be excluded as completely as possible to prevent reaction 1. It was soon found, however, that this conception was erroneous and that the role of catalyst can be played very successfully by certain organic salts, such as alkali acetates, formates, benzoates, etc., and purely inorganic carbonates, bicarbonates, sulfites, nitrites, and reaction 2 can be smoothly effected in systems containing considerable water (10%). Thus, while BzCCl3 is not changed in the least by heating 8 hrs. at 170° in a sealed tube, addition of a droplet of dilute aqueous KOH to its MeOH solution suffices to decompose it at once, with evolution of heat, into BzOMe and CHCl3, Presumably there is first formed a little BzOK which quickly exerts its powerful catalytic effect. Mg(OH)2, shaken a long time in aqueous suspension with BzCCl3, decomposes it almost completely into (BzO)2Mg and CHCl3 but in aqueous MeOH gives 92% BzOMe. Thus, in addition to the possibility of neutralizing aqueous or aqueous alc. alkali by completely neutral compounds such as AcCCl3, BzCCl3, etc., a reaction which may prove useful for preparative and anal. purposes, there is the further possibility of decomposing, also in completely neutral solution, the excess of halogen ketone by subsequent addition of alc. It may thus be possible, by addition of minute amounts of perfectly neutral substances, to produce large quantities of nascent CHCl3, CHBr3, HCN (nitriles also undergo the reaction). The milder conditions (entire absence of strong alkalies) under which reaction 2 can now be effected has made it possible to extend the reaction to other substances which previously had either not reacted at all (phenols) or only with difficulty (menthol), for long and high heating may be employed, if necessary, and the reaction can be carried out in alk., neutral or acid solution; thus, KOAc is effective in AcOH and HCO2K reacts excellently in HCO2H. Hydrolysis of the trihalomethyl ketones can likewise be effected by aqueous solutions of catalytically small quantities of certain salts or, what amounts to the same thing, of alkalies, for these are rapidly converted by the ketone into the catalytic salt. Thus, BzCCl3 is smoothly decomposed into BzOH and CHCl3 by boiling several hrs. with water to which has been added a little KOAc; with water alone there is no hydrolysis even after 7 hrs. at 170°. Reaction 1 is really based on catalytic hydrolysis, the much slower velocity of which, as compared with the catalytic esterification (reaction 2) seems to be due to the slight solubility of the hydrolysis products; its acceleration by a stoichiometric amount of alkali (reaction 1) may in great part be due to the opportunity thus afforded to the BzOH to dissolve; in aqueous Me2CO containing a trace of KOAc, 96% BzOH was obtained from BzCCl3 after refluxing 4 hrs. The ready splitting off of a C atom from the trihalomethyl ketones does not occur with the dihalogen compounds, as far as can be judged from experiments with BzCHCl2, which yields PhCH(OH)CO2H. The following % yields of ester were obtained from the appropriate trichloromethyl ketone and alc. in the presence of a little Na: m-O2NC6H4CO2Me 62, m-H2NC6H4CO2Me 90, Et 2,4-dimethylpyrrole-5-carboxylate 93, Et 2-methylindole-3-carboxylate 85, octyl acetate 70, cetyl benzoate 45. Yield of phenol esters with KOAc as catalyst (reaction temperature in parentheses): PhOBz 80 (120°), p-MeC6H4OBz 90 (230°), o-MeC6H4CO2Bz 80 (230°), menthyl benzoate 58 (150°) (the yield previously obtained with Na was 37%). Below are given, resp., the length of reaction (in days unless otherwise stated) and the % yield of benzoate obtained at 20° from BzCCl3 with various alcs. and 0.5-1 equivalent of different catalysts. MeOH: HCO2K 2, 74; HCO2K + HCO2H 3, 85; KOAc 2, 92; KOAc + AcOH 3, 90; KOBz 1, 81; KNO3 3, 91; Mg(OH)2 1, 92. PrOH: Mg(OH)2 2, 79. iso-BuOH: KOAc 4, 90. Hexyl alc.: KOAc 4, 93. Allyl alc.: KOAc 2, 93. Menthol: KOAc 6 hrs. at 150°, 58. PhOH: 4 hrs. at 120°, 80. o-Cresol: KOAc, 4 hrs. at 130°, 80. p-Cresol: KOAc 4 hrs. at 130°, 90. Although very small amounts of the catalysts are distinctly effective, 0.5-1 equivalent was used to shorten the reaction time as much as possible. The lengths of reaction given were in many cases perhaps unnecessarily long. KHCO3, Na2CO3, Na2SO3 and AcONH4 are also effective, but KNO3, anhydrous or hydrated NH4Cl, K bioxalate, HCl.H2O, H2SO4.H2O and HCl are not effective even after 1 day at 70°. BzCCl3 (2.23 g.) and 0.5 g. KOAc, allowed to stand 1 day in 5 cc. MeOH containing 10% water, gave 81% BzOMe; 2.23 g. of the ketone and 0.5 g. KOAc shaken 25 hrs. in 2.4 cc. MeOH containing 50% water gave 22% ester and 70% unchanged ketone. When BzCHCl2 was allowed to stand with 0.1 equivalent Na in MeOH the alkalinity soon greatly diminished and Cl ions but no CH2Cl2 or BzOMe were formed; with 2 equivalents Na, NaCl was deposited and after standing overnight there was obtained 61% phenylglyoxal di-Me acetal, b13 110-4°.

Compound(2199-44-2)Formula: C9H13NO2 received a lot of attention, and I have introduced some compounds in other articles, similar to this compound(Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate), if you are interested, you can check out my other related articles.

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Category: thiazolidine. 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 x-ray Crystallographic and 13C NMR Investigations of the Effects of Electron-Withdrawing Groups on a Series of Pyrroles. Author is Thompson, Alison; Gao, Susan; Modzelewska, Gosia; Hughes, David S.; Patrick, Brian; Dolphin, David.

Pyrroles substituted with various electron-withdrawing groups (EWGs) on the N atom were synthesized and full characterization including x-ray crystal structures obtained. Anal. of 13C chem. shifts and x-ray crystal structures reveals that a trend between decreased aromaticity and the strength of the EWG exists. Exptl. results regarding alternative mechanisms of nucleophilic substitution reactions can thus be rationalized.

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Formula: C9H13NO2. The mechanism of aromatic electrophilic substitution of aromatic heterocycles is consistent with that of benzene. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about A highly efficient preparation of 3,3′-dipyrrolyl sulfides. Author is Chen, Qingqi; Dolphin, David.

3,3′-Dipyrrolyl sulfides I (R = CHO, EtO2C, PhO2C, R2 = H, Me, MeO2C, EtO2C), useful building blocks for linear or cyclic polypyrrolic ligands, were prepared, in high yield, by the reaction of sulfur dichloride with 3-unsubstituted pyrroles II at low temperature

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So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic.Cauletti, Carla; Giancaspro, Carlo; Monaci, Anna; Piancastelli, M. Novella researched the compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate( cas:2199-44-2 ).Category: thiazolidine.They published the article 《Free energy relationships of ionization energies measured by ultraviolet photoelectron spectroscopy in substituted pyrroles》 about this compound( cas:2199-44-2 ) in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999). Keywords: LFER ionization energy substituted pyrrole; UPS substituted pyrrole; substituent effect photoelectron spectra pyrrole. We’ll tell you more about this compound (cas:2199-44-2).

The ionization energies of six 5-substituted-3-ethoxycarbonyl-2,4-dimethylpyrroles and seven 4-substituted 2-ethoxycarbonyl-3,5-dimethylpyrroles were determined by UPS. The relations between the lowest ionization potentials and σ were determined and the different influence of substituents in the α- and β-positions is discussed.

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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 new pyrrole synthesis》. Authors are Fischer, Hans; Fink, Emmy.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).Related Products of 2199-44-2. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

Mutual reduction of isonitrosoacetoacetic ester or isonitrosobutyryl-acetic ester and AcCH2CH(OEt)2 (I) in the presence of Zn dust yielded 2-methyl-5-carbethoxypyrrole (II), m. 100°, subliming at 90° at 20 mm. On treatment with HCN and HCl in ether, II was converted to 2-methyl-5-carbethoxy-3-pyrrolecarboxaldehyde, m. 119°. I, heated with glacial AcOH for 1/2 h., yielded triacetylbenzene (III), m. 161°. In cold glacial AcOH, III was formed in only minimal amounts from I, but in considerable amounts from the Na salt of formylacetone. Acetylacetone was condensed with isonitrosoacetoacetic ester to form 2,4-dimethyl-3-acetyl-5-carbethoxypyrrole, and as a side-product, 2,4-dimethyl-5-carbethoxypyrrole, m. 123°. Glycine was condensed with AcCH2CHO, or with I, or with the Na salt of formylacetone, to yield a product, not yet isolated, giving a pos. Ehrlich reaction for pyrrole. These syntheses may be of physiol. importance in the formation of blood pigments.

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