Category: 2199-44-2

In general, if the atoms that make up the ring contain heteroatoms, such rings become heterocycles, and organic compounds containing heterocycles are called heterocyclic compounds. An article called Synthesis of pyrrolecarboxaldehydes, published in 1956, which mentions a compound: 2199-44-2, Name is Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, Molecular C9H13NO2, Safety of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

HCO-NMe2 (I) (23.89 g.) and 58.25 g. POCl3 warmed after 10 min. to 60°, treated dropwise in 1.5 hrs. with 18 g. 2,4-dimethylpyrrole in an equal volume of I, the mixture stirred 1 hr. at 60°, poured into 333 g. ice and 245 g. fused NaOAc, the mixture boiled, cooled, extracted with Et2O, the extract evaporated free from Et2O and made alk. with powd. Na2CO3, filtered, and the residual product (II) dried. Further extraction of the filtrate with Et2O gave another 0.69 g. II. II boiled in petr. ether, the solution purified with C, filtered and cooled gave 0.6 g. (crude) 2,4-dimethyl-3,5-pyrroledicarboxaldehyde, m. 165-6° (from H2O), and 9.6 g. (crude) 2,4-dimethyl-5-pyrrolecarboxaldehyde, m. 89-90° (from H2O). Similarly, I and POCl3 at 60°, treated dropwise with stirring with 2,4-dimethyl-8-ethylpyrrole gave 2,4-dimethyl-3-ethyl-5-pyrrolecarboxaldehyde, m. 105-6°. In the same way, 1.79 g. I and 4.37 g. POCl3 treated with 1.35 g. 2,3,4-trimethylpyrrole gave 0.3 g. 2,3,4-trimethyl-5-pyrrolecarboxaldehyde, m. 147°; 2.6 g. I and 6.32 g. POCl3 with 3 g. Et 2,4-dimethyl-3-pyrrolecarboxylate in I yielded Et 2,4-dimethyl-5-formyl-3-pyrrolecarboxylate, m. 165°; 8.6 g. I and 21 g. POCl3 with 10 g. Et 2,4-dimethyl-5-pyrrolecarboxylate and 10 g. I produced 11.2 g. Et 2,4-dimethyl-3-formyl-5-pyrrolecarboxylate, m. 145°. Heating 20 g. 2,4-dimethyl-5-carbethoxy-3-pyrrolecarboxylate at 200° with 200 g. quinoline and 2 g. finely divided pure Cu to cessation of CO2 evolution, cooling, filtering, acidifying the filtrate with 50% HCl, filtering, washing the precipitate with H2O, and drying gave 11.2 g. Et 2,4-dimethyl-5-pyrrolecarboxylic acid, m. 122°.

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Thiazolidine – Wikipedia,
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Computed Properties of C9H13NO2. 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. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Fluoropyrroles and tetrafluoroporphyrins.

Photolysis of the pyrrole-β-diazonium tetrafluoroborate I (R = N2+BF4-) gave the β-fluoropyrrole I (R = F) which was oxidized to the alc. II. Treatment of II with K3Fe(CN)6 or Cu(OAc)2 gave the fluoroporphyrins III (M = 2H, Cu) resp.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Decarboxylation and formylation of certain pyrrole derivatives》. Authors are Chu, Edith Ju-Hwa; Chu, T. C..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.

H2NCH2CH2OH (I) is used as decarboxylation agent for substituted carboxypyrroles. Adding 28.5 g. AcCH2CO2Et to Et α-nitroso-α-benzoylacetate (from 38.5 g. BzCH2CO2Et), then adding gradually 28.5 g. Zn dust with gentle boiling, refluxing the mixture 2 hrs., and pouring it into H2O give 63% 2-methyl-4-phenyl-3,5-dicarbethoxypyrrole, colorless prisms, m. 124-5°. 2,4-Dimethyl-3-carboxy-5-carbethoxypyrrole (II), 85%, fine prisms, m. 272° (decomposition), and 2-methyl-4-phenyl-3-carboxy-5-carbethoxypyrrole (III), 78%, platelets, m. 220° (decomposition) are prepared by partial saponification of the corresponding diesters. Refluxing 21.1 g. II and 12.2 g. I 1 hr. and pouring the mixture into H2O give 90% 2,4-dimethyl-5-carbethoxypyrrole (IV), prisms, m. 124.5-5°; similarly, III gives 84% 2-methyl-4-phenyl-5-carbethoxypyrrole, needles, m. 134.5-5°. Gradually adding 15.4 g. POCl3 to 13.4 g. IV and 7.3 g. HCONMe2, refluxing the mixture 2 hrs., pouring it into H2O, and neutralizing it with NaOAc give 95% 2,4-dimethyl-3-formyl-5-carbethoxypyrrole, needles, m. 145-5.5° (oxime, m. 199-200°; semicarbazone, decompose at about 275°). 2-Methyl-4-phenyl-3-formyl-5-carbethoxypyrrole, prepared similarly in 97% yield, prisms, m. 144.5-5° (oxime, 96%, plates, m. 210-11°; semicarbazone, needles, decompose at about 280° with sublimation).

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Fluoropyrroles and tetrafluoroporphyrins, the main research direction is fluoropyrrole preparation cyclocondensation; fluoroporphyrin; porphyrin tetrafluoro.HPLC of Formula: 2199-44-2.

Photolysis of the pyrrole-β-diazonium tetrafluoroborate I (R = N2+BF4-) gave the β-fluoropyrrole I (R = F) which was oxidized to the alc. II. Treatment of II with K3Fe(CN)6 or Cu(OAc)2 gave the fluoroporphyrins III (M = 2H, Cu) resp.

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Reference:
Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

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, Article, Acta Crystallographica, Section E: Structure Reports Online called Ethyl 3,5-dimethyl-1H-pyrrole-2-carboxylate, Author is Arranja, Claudia T.; Ramos Silva, Manuela; Matos Beja, Ana; Ferreira, Ana F. P. V.; Sobral, Abilio J. F. N., which mentions a compound: 2199-44-2, SMILESS is O=C(C1=C(C)C=C(C)N1)OCC, Molecular C9H13NO2, Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate.

In the title compound, C9H13NO2, there are two independent mols. per asym. unit. The mols. are very similar and almost planar, with the ethoxycarbonyl group anti to the pyrrole N atom. The two independent mols. are joined into dimeric units by strong hydrogen bonds between NH groups and carbonyl O atoms. Crystallog. data are given.

There is still a lot of research devoted to this compound(SMILES：O=C(C1=C(C)C=C(C)N1)OCC)Name: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, and with the development of science, more effects of this compound(2199-44-2) can be discovered.

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 《Decarboxylation and formylation of certain pyrrole derivatives》. Authors are Chu, Edith Ju-Hwa; Chu, T. C..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).Reference of Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate. Through the article, more information about this compound (cas:2199-44-2) is conveyed.

H2NCH2CH2OH (I) is used as decarboxylation agent for substituted carboxypyrroles. Adding 28.5 g. AcCH2CO2Et to Et α-nitroso-α-benzoylacetate (from 38.5 g. BzCH2CO2Et), then adding gradually 28.5 g. Zn dust with gentle boiling, refluxing the mixture 2 hrs., and pouring it into H2O give 63% 2-methyl-4-phenyl-3,5-dicarbethoxypyrrole, colorless prisms, m. 124-5°. 2,4-Dimethyl-3-carboxy-5-carbethoxypyrrole (II), 85%, fine prisms, m. 272° (decomposition), and 2-methyl-4-phenyl-3-carboxy-5-carbethoxypyrrole (III), 78%, platelets, m. 220° (decomposition) are prepared by partial saponification of the corresponding diesters. Refluxing 21.1 g. II and 12.2 g. I 1 hr. and pouring the mixture into H2O give 90% 2,4-dimethyl-5-carbethoxypyrrole (IV), prisms, m. 124.5-5°; similarly, III gives 84% 2-methyl-4-phenyl-5-carbethoxypyrrole, needles, m. 134.5-5°. Gradually adding 15.4 g. POCl3 to 13.4 g. IV and 7.3 g. HCONMe2, refluxing the mixture 2 hrs., pouring it into H2O, and neutralizing it with NaOAc give 95% 2,4-dimethyl-3-formyl-5-carbethoxypyrrole, needles, m. 145-5.5° (oxime, m. 199-200°; semicarbazone, decompose at about 275°). 2-Methyl-4-phenyl-3-formyl-5-carbethoxypyrrole, prepared similarly in 97% yield, prisms, m. 144.5-5° (oxime, 96%, plates, m. 210-11°; semicarbazone, needles, decompose at about 280° with sublimation).

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Thiazolidine – Wikipedia,
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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 Sulfur derivatives in the pyrrole series, published in 1973, which mentions a compound: 2199-44-2, mainly applied to pyrrolyl sulfide; thiocarboxamide pyrrole, Synthetic Route of C9H13NO2.

Reaction of 2,4-dimethyl-5-(ethoxycarbonyl)pyrrole (I) with SO2 in the presence of EtBr and AlCl3 or in CH2Cl2 containing AlCl3 gave the sulfide II or the sulfoxide III, resp. Successive reaction of SCl2 with MeOH and 2-methyl-3-(ethoxycarbonyl pyrrole gave the disulfide IV. Addition of EtSH to tris[2-methyl-3-(ethoxycarbonyl)-5-pyrrolyl]methane gave the sulfide V. Addition of p-tolysulfonyl isothiocyanate to I gave the derivative VI.

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Thiazolidine – Wikipedia,
Thiazolidine – ScienceDirect.com

The chemical properties of alicyclic heterocycles are similar to those of the corresponding chain compounds. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Structure-Activity Relationships of (4-Acylpyrrol-2-yl)alkanoic Acids as Inhibitors of the Cytosolic Phospholipase A2: Variation of the Substituents in Positions 1, 3, and 5, the main research direction is acylpyrrole alkanoate inhibitor preparation phospholipase A2.Application of 2199-44-2.

Derivatives of 3-(1,3,5-trimethyl-4-octadecanoylpyrrol-2-yl)propionic acid (1) and (1,3,5-trimethyl-4-octadecanoylpyrrol-2-yl)acetic acid (4) were prepared and evaluated for their ability to inhibit the cytosolic phospholipase A2 of intact bovine platelets. While replacement of one of the Me groups in position 1, 3, or 5 of the acetic acid 4 by a benzyl residue did not influence the inhibitory potency significantly, the introduction of a dodecyl chain led to compounds which even enhanced the enzymic activity. Stepwise elongation of the alkyl substituent in position 1 showed that the ability to inhibit the enzyme was lost when the alkyl chain exceeded a length of five carbons in case of compound 1 or six carbons in case of compound 4. Introduction of a polar functional group at the end of the 1-alkyl chain of these inactive pyrroles, however, restored or even elevated inhibitory potency. The most preferable of the polar terminal functions investigated was the carboxylic acid moiety. 6-[2-(2-Carboxyethyl)-4-dodecanoyl-3,5-dimethylpyrrol-1-yl]hexanoic acid (65c) and 6-[2-(carboxymethyl)-4-dodecanoyl-3,5-dimethylpyrrol-1-yl]nonanoic acid (66f) were to the synthesized inhibitors with the greatest potency. With IC50 values of 3.4 and 3.3 μM, resp., they were about 3-fold more active than the standard cPLA2 inhibitor arachidonyl trifluoromethyl ketone (IC50: 11 μM).

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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).COA of 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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Synthetic Route of C9H13NO2. 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. Compound: Ethyl 3,5-Dimethyl-2-pyrrolecarboxylate, is researched, Molecular C9H13NO2, CAS is 2199-44-2, about Synthesis of novel tetrapyrroles and their zinc complexes.

2,2′-Tetramethyl-5,5′-bis(ethoxycarbonyl)-3,3′-dipyrromethane, prepared from 3,5-dimethyl-2-ethoxycarbonyl-1H-pyrrole and paraformaldehyde, was converted to the dicarboxylic acid and subsequently to the dialdehyde which was reacted with tert-butoxy 4-ethyl-3,5-dimethylpyrazole-2-carboxylate/3,4-diethyl-5-methylpyrazole-2-carboxylic acid/3,5-dimethyl-4-methoxycarbonylethylpyrrole-2-carboxylic acid to give I.2HBr (R = Me, R1 = Et or R = R1 = Et or R = Me, R1 = CH2CH2COOMe). I (R = Me, R1 = Et or CH2CH2COOMe) (HL) reacted with Zn(OAc)2 to give ZnL2.

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