3-Nitrobenzaldehyde → HCID 68120470, compound

HRID 1283291Notes

Reaction equation

HRID 1283291 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:22])/[CH:16]=[C:17](\[NH2:21])/[CH2:18][O:19][CH3:20])[CH3:13].[CH2:23]([O:25][C:26](=[O:35])[CH2:27][C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])=O)[CH3:24]>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:27]([C:26]([O:25][CH2:23][CH3:24])=[O:35])=[C:28]([C:30]([O:32][CH2:33][CH3:34])=[O:31])[NH:21][C:17]=1[CH2:18][O:19][CH3:20])=[O:22])[CH3:13]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 66951Diethyl oxalacetateHCID 45122131HCID 45122131, compound

Product 1

HCID 68120470HCID 68120470, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

After heating a solution of 15.1 g of 3-nitrobenzaldehyde, 16 g of β-amino-γ-methoxycrotonic acid ethyl ester and 19 g of oxalacetic acid diethyl ester in 60 ml of ethanol under reflux for 12 hours, the mixture is evaporated in vacuo and 2-methoxymethyl-4-(3'-nitrophenyl)-1,4-dihydropyridine-3,5,6-tricarboxylic acid triethyl ester is obtained in almost quantitative yield, in the form of a yellow oil (nD50 =1.5353).

Workup

  1. temperatureunder reflux for 12 hours
  2. customthe mixture is evaporated in vacuo

Sources & evidence

ORD record
ord-b02d2de759c24ac0b8ac8b8bb57d1ec9
Source dataset
uspto-grants-1976_08
Patent number
US03974278

Reaction notes

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