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

HRID 918501Notes

Reaction equation

HRID 918501 reaction equation
C(OC(=O)C[C:6]([CH:8]=[CH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[C:16]#[N:17])=[O:7])C.[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)[CH3:30].[CH2:33](O)[CH3:34]>>[CH2:29]([O:32][C:6]([C:8]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]#[N:17])[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:7])[CH3:30]

Participants

5

Reactant 4

HCID 702EthanolHCID 3776IsopropanolHCID 12391080Amidinoacetic acid isopropyl esterHCID 543164072-Cyanobenzylideneacetoacetic acid ethyl ester

Product 1

HCID 706361682-Amino-6-methyl-4-(2-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-ethyl esterYield 58%

Procedure

Upon boiling a solution of 12.2 g of 2-cyanobenzylideneacetoacetic acid ethyl ester and 7.2 g of amidinoacetic acid isopropyl ester in 200 ml of ethanol for 1 hour, 2-amino-6-methyl-4-(2-cyanophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-ethyl ester of melting point 200°C (isopropanol) is obtained. Yield: 58% of theory.

Workup

  1. customfor 1 hour

Sources & evidence

ORD record
ord-e52f77cfd2554abfaebc455f57d9b875
Source dataset
uspto-grants-1976_07
Patent number
US03971791

Reaction notes

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