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

HRID 1414418Notes

Reaction equation

HRID 1414418 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[N+:16]([O-:18])=[O:17])=[O:7])C.[CH:20]([O:23][C:24](=[O:29])[CH2:25][C:26](=[NH:28])[NH2:27])([CH3:22])[CH3:21].[CH:30]([OH:33])(C)[CH3:31].[CH2:34](O)[CH3:35]>>[CH2:30]([O:33][C:6]([C:8]1[CH:9]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[N+:16]([O-:18])=[O:17])[C:25]([C:24]([O:23][CH:20]([CH3:22])[CH3:21])=[O:29])=[C:26]([NH2:27])[NH:28][C:34]=1[CH3:35])=[O:7])[CH3:31]

Participants

5

Reactant 4

HCID 702EthanolHCID 3776IsopropanolHCID 12391080Amidinoacetic acid isopropyl esterHCID 53923751Ethyl 2-nitrobenzylidene-acetoacetate

Product 1

HCID 706351172-Amino-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-ethyl esterYield 39%

Procedure

Boiling a solution of 13.2 g of 2-nitrobenzylideneacetoacetic acid ethyl ester and 7.2 g of amidinoacetic acid isopropyl ester in 100 ml of ethanol for 6 hours yields 2-amino-6-methyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-isopropyl ester 5-ethyl ester of melting point 139°C (isopropanol).

Workup

  1. customfor 6 hours

Sources & evidence

ORD record
ord-452e9b44b69149b6b8ff77c11dec48f4
Source dataset
uspto-grants-1977_01
Patent number
US04001258

Reaction notes

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