Benzyl 5-cyano-2-(trifluoromethyl)benzoate → 5-(Aminomethyl)-2-(trifluoromethyl)benzoic acid

HRID 889532Notes

Reaction equation

HRID 889532 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([C:19]([F:22])([F:21])[F:20])=[C:7]([CH:18]=1)[C:8]([O:10]CC1C=CC=CC=1)=[O:9])#[N:2].[H][H]>[Pd].CO>[NH2:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([C:19]([F:20])([F:21])[F:22])=[C:7]([CH:18]=1)[C:8]([OH:10])=[O:9]

Participants

5

Reactant 2

HCID 67970345Benzyl 5-cyano-2-(trifluoromethyl)benzoateHCID 178418361HCID 178418361, compound

Product 1

HCID 679706675-(Aminomethyl)-2-(trifluoromethyl)benzoic acidYield 50%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Combine benzyl 5-cyano-2-(trifluoromethyl)benzoate (3.9 g, 12.78 mmol, 1.0 equiv), palladium (10 wt % on carbon, 400 mg, 0.38 mmol, 0.03 equiv), and methanol (128 mL), and purge the mixture with hydrogen. Stir overnight under a hydrogen atmosphere. Filter the mixture through a pad of diatomaceous earth, and then rinse the pad with hot methanol (3×150 mL) to bring through precipitated product. Concentrate the filtrate under reduced pressure to give the title compound (1.4 g, 50%). MS (m/z) 220 (M+1).

Workup

  1. filtrationFilter the mixture through a pad of diatomaceous earth
  2. washrinse the pad with hot methanol (3×150 mL)
  3. customto bring through precipitated product
  4. concentrationConcentrate the filtrate under reduced pressure

Sources & evidence

ORD record
ord-21675f574bca4d0eadccd8c716c51bfa
Source dataset
uspto-grants-2012_08
Patent number
US08252831B2

Reaction notes

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