2-Chlorobenzylideneacetone → Ethyl 2-amino-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3-carboxylate

HRID 1729688Notes

Reaction equation

HRID 1729688 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[CH:4]=[CH:5][C:6](=O)[CH3:7].[CH2:13]([O:15][C:16](=[O:21])[CH2:17][C:18](=[NH:20])[NH2:19])[CH3:14]>C(O)C>[CH2:13]([O:15][C:16]([C:17]1[CH:4]([C:3]2[CH:9]=[CH:10][CH:11]=[CH:12][C:2]=2[Cl:1])[CH:5]=[C:6]([CH3:7])[NH:20][C:18]=1[NH2:19])=[O:21])[CH3:14]

Participants

4

Reactant 2

HCID 1407602-ChlorobenzylideneacetoneHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 193867Ethyl 2-amino-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyridine-3-carboxylateYield 62%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon boiling a solution of 18.1 g of 2-chlorobenzylideneacetone and 13.0 g of amidinoacetic acid ethyl ester in 150 ml of ethanol for 2 hours, 2-amino-6-methyl-4-(2-chlorophenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester of melting point 171°C (ethanol) is obtained. Yield: 62 percent of theory.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-0b6573f82fd3413a8df7fabbea891dda
Source dataset
uspto-grants-1976_11
Patent number
US03989708

Reaction notes

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