3-Nitrobenzaldehyde → HCID 68121035, compound

HRID 918444Notes

Reaction equation

HRID 918444 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:23])[CH2:16][C:17]([CH2:19][O:20][CH2:21][CH3:22])=O)[CH3:13].[CH2:24]([O:26][C:27](=[O:32])/[CH:28]=[C:29](\[NH2:31])/[CH3:30])[CH3:25]>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:28]([C:27]([O:26][CH2:24][CH3:25])=[O:32])=[C:29]([CH3:30])[NH:31][C:17]=1[CH2:19][O:20][CH2:21][CH3:22])=[O:23])[CH3:13]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-HCID 3016245Ethyl 4-ethoxy-3-oxobutyrate

Product 1

HCID 68121035HCID 68121035, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

15 g of 3-nitrobenzaldehyde, 18 g of γ-ethoxyacetoacetic acid ethyl ester and 13 g of β-aminocrotonic acid ethyl ester are heated in 60 ml of ethanol for about 5 hours, the mixture is cooled and the product is filtered off and rinsed with cold ethanol. 2-Ethoxymethyl-6-methyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylic acid diethyl ester is obtained, in the form of light yellow crystals of melting point 120°-122°C, in a yield of 70% of theory.

Workup

  1. temperaturethe mixture is cooled
  2. filtrationthe product is filtered off
  3. washrinsed with cold ethanol

Sources & evidence

ORD record
ord-13645abec30c4522ab7546f693f595d3
Source dataset
uspto-grants-1976_07
Patent number
US03971796

Reaction notes

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