(1,1'-Biphenyl)-2-carboxaldehyde → 2,6-Diamino-4-(biphenyl-2-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 328223

Reaction equation

HRID 328223 reaction equation
[C:1]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:2]([CH:7]=O)=[CH:3][CH:4]=[CH:5][CH:6]=1.[CH2:15]([O:17][C:18](=[O:23])[CH2:19][C:20](=[NH:22])[NH2:21])[CH3:16]>C(O)C>[CH2:15]([O:17][C:18]([C:19]1[CH:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][C:1]=2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:19]([C:18]([O:17][CH2:15][CH3:16])=[O:23])=[C:20]([NH2:21])[NH:22][C:20]=1[NH2:21])=[O:23])[CH3:16]

Participants

4

Reactant 2

HCID 121052(1,1'-Biphenyl)-2-carboxaldehydeHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 706316442,6-Diamino-4-(biphenyl-2-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl esterYield 33%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon heating a solution of 9.1 g biphenyl-2-aldehyde and 13.0 g amidinoacetic acid ethyl ester in 200 ml ethanol for two hours, 2,6-diamino-4-(biphenyl-2-yl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester of m.p. 215° (ethanol) is obtained.

Sources & evidence

ORD record
ord-cca57af9b6a948d3bc0cac57d86293ef
Source dataset
uspto-grants-1977_04
Patent number
US04016277

Linked notes

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