3-Nitrobenzaldehyde → HCID 14052066, compound

HRID 986451Notes

Reaction equation

HRID 986451 reaction equation
[C:1]([O:7][CH2:8][CH2:9][O:10][CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][CH:15]=1)(=[O:6])[CH2:2][C:3]([CH3:5])=O.[NH2:27]/[C:28](/[CH3:34])=[CH:29]\[C:30]([O:32][CH3:33])=[O:31].[N+:35]([C:38]1[CH:39]=[C:40]([CH:43]=[CH:44][CH:45]=1)[CH:41]=O)([O-:37])=[O:36]>C(O)C>[CH3:5][C:3]1[NH:27][C:28]([CH3:34])=[C:29]([C:30]([O:32][CH3:33])=[O:31])[CH:41]([C:40]2[CH:43]=[CH:44][CH:45]=[C:38]([N+:35]([O-:37])=[O:36])[CH:39]=2)[C:2]=1[C:1]([O:7][CH2:8][CH2:9][O:10][CH2:11]/[CH:12]=[CH:13]/[C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:22]=[N:23][CH:24]=[CH:25][CH:26]=2)=[CH:16][CH:15]=1)=[O:6]

Participants

5

Reactant 3

HCID 74493-NitrobenzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 14099895HCID 14099895, compound

Product 1

HCID 14052066HCID 14052066, compoundYield 60.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 10 ml of ethanol were dissolved 1.0 g of 2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyloxy]ethyl acetoacetate, 330 mg of methyl 3-aminocrotonate and 430 mg of 3-nitrobenzaldehyde, and the resulting solution was subjected to reaction under reflux for 9 hours. Subsequently, the solvent was removed by distillation under reduced pressure, and the residue thus obtained was purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (1:1 by volume)] to obtain 1.0 g (yield 60.6%) of yellow, oily 3-[2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyloxy]ethyl] 5-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. customthe resulting solution was subjected to reaction
  2. temperatureunder reflux for 9 hours
  3. customSubsequently, the solvent was removed by distillation under reduced pressure
  4. customthe residue thus obtained
  5. customwas purified by a column chromatography [Wako Silica Gel C-200, eluant: toluene:ethyl acetate (1:1 by volume)]

Sources & evidence

ORD record
ord-05f7e15ff20f4ae7a6b29f665970782d
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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