3-Nitrobenzaldehyde → 2-Acetoxymethyl-6-methyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

HRID 1449001Notes

Reaction equation

HRID 1449001 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].[CH2:12]([O:14][C:15](=[O:24])[CH2:16][C:17]([CH2:19][O:20][C:21](=[O:23])[CH3:22])=O)[CH3:13].[CH2:25]([O:27][C:28](=[O:33])/[CH:29]=[C:30](\[NH2:32])/[CH3:31])[CH3:26]>C(O)C>[CH2:12]([O:14][C:15]([C:16]1[CH:7]([C:6]2[CH:9]=[CH:10][CH:11]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=2)[C:29]([C:28]([O:27][CH2:25][CH3:26])=[O:33])=[C:30]([CH3:31])[NH:32][C:17]=1[CH2:19][O:20][C:21](=[O:23])[CH3:22])=[O:24])[CH3:13]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 11480907Ethyl 4-acetoxyacetoacetate

Product 1

HCID 133883462-Acetoxymethyl-6-methyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

7.5 g of 3-nitrobenzaldehyde, 9.4 g of γ-acetoxyacetoacetic acid ethyl ester and 6.5 g of β-aminocrotonic acid ethyl ester in 40 ccs of ethanol are heated under reflux for 20 hours, the mixture is cooled and the precipitate is filtered off.

Workup

  1. temperatureunder reflux for 20 hours
  2. temperaturethe mixture is cooled
  3. filtrationthe precipitate is filtered off

Sources & evidence

ORD record
ord-6fecc888405549d1a07bffdb9dc092f3
Source dataset
uspto-grants-1980_02
Patent number
US04188395

Reaction notes

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