Isopropanol → 2-Amino-6-methyl-4-(3-chlorophenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester

HRID 1729690Notes

Reaction equation

HRID 1729690 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[CH:5]=[CH:6][C:7](=O)[CH3:8].[CH2:13]([O:15][C:16](=[O:21])[CH2:17][C:18](=[NH:20])[NH2:19])[CH3:14].C(O)(C)C>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[CH:5]([C:4]2[CH:10]=[CH:11][CH:12]=[C:2]([Cl:1])[CH:3]=2)[CH:6]=[C:7]([CH3:8])[NH:20][C:18]=1[NH2:19])=[O:21])[CH3:14]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 1415763-ChlorobenzylideneacetoneHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 123910982-Amino-6-methyl-4-(3-chlorophenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After heating a solution of 18.1 g of 3-chlorobenzylideneacetone and 13.0 g of amidinoacetic acid ethyl ester in 150 ml of ethanol for 3 hours, 2-amino-6-methyl-4-(3-chlorophenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester of melting point 140°C (isopropanol) is obtained. Yield: 56 percent of theory.

Sources & evidence

ORD record
ord-6e3af589c7304c3f9b0ebdbd8f479363
Source dataset
uspto-grants-1976_11
Patent number
US03989708

Reaction notes

Loading…