3-(Trifluoromethyl)benzaldehyde → HCID 14052070, compound

HRID 986452Notes

Reaction equation

HRID 986452 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].[F:35][C:36]([F:46])([F:45])[C:37]1[CH:38]=[C:39]([CH:42]=[CH:43][CH:44]=1)[CH:40]=O>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:40]([C:39]2[CH:42]=[CH:43][CH:44]=[C:37]([C:36]([F:35])([F:45])[F:46])[CH:38]=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 679903-(Trifluoromethyl)benzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 14099895HCID 14099895, compound

Product 1

HCID 14052070HCID 14052070, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 5 ml of ethanol were dissolved 500 mg of 2-[(E)-3-[4-(3-pyridylmethyl)phenyl]allyloxy]ethyl acetoacetate, 0.20 g of methyl 3-aminocrotonate and 300 mg of 3-trifluoromethylbenzaldehyde, and the resulting solution was subjected to reaction under reflux for 15 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: chloroform:ethanol (100:1 by volume)] to obtain 660 mg (yield 72.8%) of pale yellow, powdery 3-[2-[(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyloxy]ethyl] 5-methyl 2,6-dimethyl-4-(3-trifluoromethylphenyl)-1,4-dihydropyridine-3,5-dicarboxylate.

Workup

  1. customthe resulting solution was subjected to reaction
  2. temperatureunder reflux for 15 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: chloroform:ethanol (100:1 by volume)]

Sources & evidence

ORD record
ord-d5fb78c5b880467595c5adc68b3c4435
Source dataset
uspto-grants-1987_12
Patent number
US04713387

Reaction notes

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