Ethanol → 2-Amino-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-methyl ester

HRID 2397900Notes

Reaction equation

COC(=O)C[C:5]([CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])=[O:6].[CH:19]([O:22][C:23](=[O:28])[CH2:24][C:25](=[NH:27])[NH2:26])([CH3:21])[CH3:20].[CH:29]([OH:32])(C)C.[CH2:33](O)[CH3:34]>>[CH3:29][O:32][C:5]([C:7]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[C:24]([C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[O:28])=[C:25]([NH2:26])[NH:27][C:33]=1[CH3:34])=[O:6]

Participants

Reactant 4

HCID 702Ethanol

HCID 3776Isopropanol

HCID 12391080Amidinoacetic acid isopropyl ester

HCID 53723829Methyl 5-(2-nitrophenyl)-3-oxopent-4-enoate

Product 1

HCID 706357232-Amino-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-methyl esterYield 50%

Procedure

Upon heating a solution of 12.5 g of 2-nitrobenzylideneacetoacetic acid methyl ester and 7.2 g of amidinoacetic acid isopropyl ester in 100 ml of ethanol for 8 hours, 2-amino-6-methyl-4-(2 -nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-methyl ester of melting point 203° C. (isopropanol) is obtained. Yield: 50% of theory.

Sources & evidence

ORD record: ord-516b89b9474648d79ff59c03bf3b7206
Source dataset: uspto-grants-1977_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04022898

Reaction notes

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