Benzylidene-benzoylacetic acid ethyl ester → 2-Amino-4,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylic acid ethyl ester

HRID 1581027Notes

Reaction equation

HRID 1581027 reaction equation
C([O:3][C:4](=[O:21])[C:5](=[CH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:6](=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)C.[CH2:22]([O:24][C:25](=[O:30])[CH2:26][C:27](=[NH:29])[NH2:28])[CH3:23]>C(O)C>[CH2:22]([O:24][C:25]([C:26]1[CH:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:5]([C:4]([OH:3])=[O:21])=[C:14]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[NH:28][C:27]=1[NH2:29])=[O:30])[CH3:23]

Participants

4

Reactant 2

HCID 140230Benzylidene-benzoylacetic acid ethyl esterHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 706355272-Amino-4,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylic acid ethyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon boiling a solution of 14.0 g of benzylidenebenzoylacetic acid ethyl ester and 6.5 g of amidinoacetic acid ethyl ester in 150 ml of ethanol for 2 hours, 2-amino-4,6-diphenyl-1,4-dihydropyridine-3,5-dicarboxylic acid ethyl ester of melting point 183°C (ethanol) is obtained.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-3f9b33dafc21492395c7408a5865e102
Source dataset
uspto-grants-1976_01
Patent number
US03935223

Reaction notes

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