3-Nitrobenzaldehyde → 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-cyanoethyl) 5-methyl ester

HRID 34411Notes

Reaction equation

HRID 34411 reaction equation
O=[C:2]([CH3:11])[CH2:3][C:4]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[O:5].[NH2:12]/[C:13](/[CH3:19])=[CH:14]\[C:15]([O:17][CH3:18])=[O:16].[N+:20]([C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH:26]=O)([O-:22])=[O:21]>CO>[CH3:19][C:13]1[NH:12][C:2]([CH3:11])=[C:3]([C:4]([O:6][CH2:7][CH2:8][C:9]#[N:10])=[O:5])[CH:26]([C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([N+:20]([O-:22])=[O:21])[CH:24]=2)[C:14]=1[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 123604062-Cyanoethyl 3-oxobutanoate

Product 1

HCID 109160093,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, 3-(2-cyanoethyl) 5-methyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 2-cyanoethy 3-oxobutanoate (83.3 g, 0.54 mol), methyl 3-aminocrotonate (61.9 g, 0.54 mol), and 3-nitrobenzaldehyde (81.3 g, 0.54 mol) in methanol (540 mL ) was heated at reflux for 8 hours, then stirred overnight. The resulting precipitate was filtered, washed with methanol, and dried to produce racemic 2,6-dimethyl-3-carbomethoxy-4-(3-nitrophenyl)-5-(2-cyano)ethoxycarbonyl-1,4-dihydropyridine (mp=123° C.).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 8 hours
  3. filtrationThe resulting precipitate was filtered
  4. washwashed with methanol
  5. customdried

Sources & evidence

ORD record
ord-b135d78203c9446597fb1623655ecbc0
Source dataset
uspto-grants-1988_08
Patent number
US04761420

Reaction notes

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