3-Nitrobenzaldehyde → Nicardipine Impurity 19

Reaktionsgleichung

[C:1]([O-:7])(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:8]/[C:9](/[CH3:18])=[CH:10]\[C:11]([O:13][CH2:14][CH2:15][C:16]#[N:17])=[O:12].[N+:19]([C:22]1[CH:23]=[C:24]([CH:27]=[CH:28][CH:29]=1)[CH:25]=O)([O-:21])=[O:20]>C(O)(C)C>[C:16]([CH2:15][CH2:14][O:13][C:11]([C:10]1[CH:25]([C:24]2[CH:27]=[CH:28][CH:29]=[C:22]([N+:19]([O-:21])=[O:20])[CH:23]=2)[C:2]([C:1]([OH:7])=[O:6])=[C:3]([CH3:5])[NH:8][C:9]=1[CH3:18])=[O:12])#[N:17]

Komponenten

Versuchsvorschrift

10.3 g of 3-nitratopropyl acetoacetate, 7.7 g of 2-cyanoethyl 3-aminocrotonate and 7.6 g of 3-nitrobenzaldehyde in 76 ml of isopropyl alcohol were heated at reflux for 6.5 hours, and cooled on ice. The crystals which precipitated were collected by filtration, dried, applied to a silica gel column chromatography (eluent: dichloromethane) and recrystallized from ethanol to give 16.4 g of 2,6-dimethyl-4-(3-nitrophenyl)1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester 5-(3-nitratopropyl) ester.