3-Nitrobenzaldehyde → 2-Amino-5-acetyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester

HRID 1581025Notes

Reaction equation

HRID 1581025 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][CH:11]=1)[CH:7]=O)([O-:3])=[O:2].[C:12]([CH2:15][C:16](=[O:18])[CH3:17])(=O)[CH3:13].[CH2:19]([O:21][C:22](=[O:27])[CH2:23][C:24](=[NH:26])[NH2:25])[CH3:20]>C(O)C>[CH2:19]([O:21][C:22]([C:23]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:15]([C:16](=[O:18])[CH3:17])=[C:12]([CH3:13])[NH:25][C:24]=1[NH2:26])=[O:27])[CH3:20]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 31261AcetylacetoneHCID 4599837Carbamimidoyl-acetic acid ethyl ester

Product 1

HCID 127169382-Amino-5-acetyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl esterYield 48%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Upon boiling a solution of 7.6 g of 3-nitrobenzaldehyde, 5.0 g of acetylacetone and 6.5 g of amidinoacetic acid ethyl ester in 100 ml of ethanol for 2 hours, 2-amino-5-acetyl-6-methyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3-carboxylic acid ethyl ester of melting point 217°C (ethanol) is obtained.

Workup

  1. customfor 2 hours

Sources & evidence

ORD record
ord-44796d07a28445f5ae8a20e95aeb6690
Source dataset
uspto-grants-1976_01
Patent number
US03935223

Reaction notes

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