Ethyl 2-cyano-3-(2-nitrophenyl)prop-2-enoate → 2,6-Diamino-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-isopropyl ester 5-ethyl ester

HRID 328225Notes

Reaction equation

HRID 328225 reaction equation
[CH2:1]([O:3][C:4](=[O:18])[C:5](=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[N+:15]([O-:17])=[O:16])[C:6]#[N:7])[CH3:2].[CH:19]([O:22][C:23](=[O:28])[CH2:24][C:25](=[NH:27])[NH2:26])([CH3:21])[CH3:20].CC[O-].[Na+]>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[CH:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[N+:15]([O-:17])=[O:16])[C:24]([C:23]([O:22][CH:19]([CH3:21])[CH3:20])=[O:28])=[C:25]([NH2:26])[NH:27][C:6]=1[NH2:7])=[O:18])[CH3:2]

Participants

5

Reactant 3

HCID 231461Ethyl 2-cyano-3-(2-nitrophenyl)prop-2-enoateHCID 2723922Sodium ethoxideHCID 12391080Amidinoacetic acid isopropyl ester

Product 1

HCID 706316142,6-Diamino-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-isopropyl ester 5-ethyl esterYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Upon heating a solution of 12.3 g 2-nitrobenzylidenecyanoacetic 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-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid-3-isopropyl ester 5-ethyl ester of m.p. 110° C is obtained.

Sources & evidence

ORD record
ord-f2958db8283c48a29905e05bd38b76e0
Source dataset
uspto-grants-1977_04
Patent number
US04016277

Reaction notes

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