Ethyl benzylidenecyanoacetate → 2,6-Diamino-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester 5-isopropyl ester

HRID 1077271

Reaction equation

HRID 1077271 reaction equation
[CH2:1]([O:3][C:4](=[O:15])[C:5](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:6]#[N:7])[CH3:2].[CH:16]([O:19][C:20](=[O:25])[CH2:21][C:22](=[NH:24])[NH2:23])([CH3:18])[CH3:17].CC[O-].[Na+]>C(O)C>[CH:16]([O:19][C:20]([C:21]1[CH:8]([C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)[C:5]([C:4]([O:3][CH2:1][CH3:2])=[O:15])=[C:6]([NH2:7])[NH:24][C:22]=1[NH2:23])=[O:25])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 74845Ethyl benzylidenecyanoacetateHCID 2723922Sodium ethoxideHCID 12391080Amidinoacetic acid isopropyl ester

Product 1

HCID 706318412,6-Diamino-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester 5-isopropyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon heating a solution of 10.1 g benzylidenecyanoacetic acid ethyl ester, 7.2 g amidinoacetic acid isopropyl ester and 0.6 g sodium ethylate in 150 ml ethanol for four hours, 2,6-diamino-4-phenyl-1,4-dihydropyridine-3,5-dicarboxylic acid 3-ethyl ester 5-isopropyl ester of m.p. 170° is obtained.

Sources & evidence

ORD record
ord-25c43c571116497abed3e41dcccb9ec9
Source dataset
uspto-grants-1976_05
Patent number
US03959474

Linked notes

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