o-(Trifluoromethyl)benzaldehyde → HCID 20250823, compound

HRID 1284910Notes

Reaction equation

HRID 1284910 reaction equation
[F:1][C:2]([F:12])([F:11])[C:3]1[CH:10]=[CH:9][CH:8]=[CH:7][C:4]=1[CH:5]=O.[C:13]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][Cl:24])(=[O:18])[CH2:14][C:15]([CH3:17])=O.[NH2:25]/[C:26](/[CH3:32])=[CH:27]\[C:28]([O:30][CH3:31])=[O:29]>C(O)(C)C>[CH3:17][C:15]1[NH:25][C:26]([CH3:32])=[C:27]([C:28]([O:30][CH3:31])=[O:29])[CH:5]([C:4]2[CH:7]=[CH:8][CH:9]=[CH:10][C:3]=2[C:2]([F:12])([F:11])[F:1])[C:14]=1[C:13]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][Cl:24])=[O:18]

Participants

5

Reactant 3

HCID 123067o-(Trifluoromethyl)benzaldehydeHCID 643918Methyl 3-aminocrotonateHCID 20250815HCID 20250815, compound

Product 1

HCID 20250823HCID 20250823, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

13.2 Grams of o-trifluoromethylbenzaldehyde, 14.6 g of 4-chlorobutyl acetoacetate and 8.8 g of methyl 3-aminocrotonate were added to 50 ml of isopropanol, and the whole mixture was refluxed by heating for 4 hours. The reaction mixture was concentrated, and the residue was purified by a silica gel column chromatography (eluant=chloroform) to yield 18.2 g of 4-chlorobutyl methyl 1,4-dihydro-2,6-dimethyl-4-(2-trifluoromethylphenyl)pyridine-3,5-dicarboxylate in the form of yellow oily substance.

Workup

  1. temperaturethe whole mixture was refluxed
  2. temperatureby heating for 4 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue was purified by a silica gel column chromatography (eluant=chloroform)

Sources & evidence

ORD record
ord-b4b105fdf9694e1e856d682112ad45d9
Source dataset
uspto-grants-1986_01
Patent number
US04564619

Reaction notes

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