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

HRID 2163726Notes

Reaction equation

HRID 2163726 reaction equation
COC(=O)C[C:5]([CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[O:6].[CH2:19]([O:21][C:22](=[O:29])[CH:23]=[C:24]([NH2:28])[N:25]([CH3:27])[CH3:26])[CH3:20].[CH:30]([OH:33])(C)C.[CH2:34](O)[CH3:35]>>[CH3:30][O:33][C:5]([CH:7]1[C:34]([CH3:35])=[N:28][C:24]([N:25]([CH3:27])[CH3:26])=[C:23]([C:22]([O:21][CH2:19][CH3:20])=[O:29])[CH:8]1[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([N+:15]([O-:17])=[O:16])[CH:10]=1)=[O:6]

Participants

5

Reactant 4

HCID 702EthanolHCID 3776IsopropanolHCID 534430103-Nitrobenzylideneacetoacetic acid methyl esterHCID 867334643-Amino-3-dimethylaminoacrylic acid ethyl ester

Product 1

HCID 706080742-Dimethylamino-6-methyl-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-methyl esterYield 54%

Procedure

Boiling a solution of 12.5 g of 3-nitrobenzylideneacetoacetic acid methyl ester and 8.2 g of 3-amino-3-dimethylaminoacrylic acid ethyl ester in 100 ml of ethanol for 2 hours yields 2-dimethylamino-6-methyl-4-(3-nitrophenyl)-4,5-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester-5-methyl ester of melting point 95° C. (isopropanol).

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-b19f45edbed74904b947877a4f6c67b1
Source dataset
uspto-grants-1979_01
Patent number
US04136187

Reaction notes

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