2-Nitrobenzaldehyde → 2,6-Dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester

HRID 568936Notes

Reaction equation

HRID 568936 reaction equation
[NH2:1]/[C:2](/[CH3:7])=[CH:3]\[C:4]([O-:6])=[O:5].[C:8]([O:14][CH2:15][CH2:16][C:17]#[N:18])(=[O:13])[CH2:9][C:10]([CH3:12])=O.[N+:19]([C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O)([O-:21])=[O:20]>C(O)(C)C>[C:17]([CH2:16][CH2:15][O:14][C:8]([C:9]1[CH:24]([C:23]2[CH:26]=[CH:27][CH:28]=[CH:29][C:22]=2[N+:19]([O-:21])=[O:20])[C:3]([C:4]([OH:6])=[O:5])=[C:2]([CH3:7])[NH:1][C:10]=1[CH3:12])=[O:13])#[N:18]

Participants

5

Reactant 3

HCID 111012-NitrobenzaldehydeHCID 123604062-Cyanoethyl 3-oxobutanoateHCID 222503863-Aminocrotonate

Product 1

HCID 867420322,6-Dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) esterYield 86.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

10.2 g of 3-nitratopropyl 3-aminocrotonate, 7.8 g of 2-cyanoethyl acetoacetate and 7.7 g of 2-nitrobenzaldehyde in 77 ml of isopropyl alcohol were heated at reflux for 8 hours, and the isopropyl alcohol was evaporated under reduced pressure. The residue was applied to a silica gel column chromatography (eluent: dichloromethane) and recrystallized from a mixture of dichloromethane and diethyl ether to give 16.2 g of 2,6-dimethyl-4-(2-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-(2-cyanoethyl) ester 5-(3-nitratopropyl) ester.

Workup

  1. temperatureat reflux for 8 hours
  2. customthe isopropyl alcohol was evaporated under reduced pressure
  3. customrecrystallized from a mixture of dichloromethane and diethyl ether

Sources & evidence

ORD record
ord-b786ef0baf864bd7bb3ee2087549c7b0
Source dataset
uspto-grants-1988_03
Patent number
US04730052

Reaction notes

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