Methanol → Methyl 2-(4-fluoroanilino)-4-(3-phenylpropyl)benzoate

HRID 2191694Notes

Reaction equation

HRID 2191694 reaction equation
CO.[F:3][C:4]1[CH:29]=[CH:28][C:7]([NH:8][C:9]2[CH:18]=[C:17]([CH:19]=[CH:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:6][CH:5]=1>[C].[Pd].C(OCC)(=O)C>[F:3][C:4]1[CH:5]=[CH:6][C:7]([NH:8][C:9]2[CH:18]=[C:17]([CH2:19][CH2:20][CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=[CH:15][C:10]=2[C:11]([O:13][CH3:14])=[O:12])=[CH:28][CH:29]=1

Participants

5

Reactant 2

HCID 887MethanolHCID 68959273Methyl 2-(4-fluoroanilino)-4-(3-phenyl-1-propenyl)benzoate

Product 1

HCID 57668036Methyl 2-(4-fluoroanilino)-4-(3-phenylpropyl)benzoate

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a mixed solution of methanol 8 mL and ethyl acetate 2 mL of the obtained methyl 2-(4-fluoroanilino)-4-(3-phenyl-1-propenyl)benzoate, 5% palladium-carbon 0.060 g was added, and it was stirred under hydrogen atmosphere at room temperature for 1 hour. Insoluble matter of the reaction mixture was filtrated, and the solvent was removed under reduced pressure. The obtained residue was refined by silica gel column chromatography [Trikonex company, Flash Tube 2008, eluent; hexane:ethyl acetate=10:1] to give methyl 2-(4-fluoroanilino)-4-(3-phenylpropyl)benzoate 0.10 g of colorless oil.

Workup

  1. filtrationInsoluble matter of the reaction mixture was filtrated
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-9e014caddec4499ab6789671acbd7694
Source dataset
uspto-grants-2012_12
Patent number
US08327467B2

Reaction notes

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