3-Nitro-5-(trifluoromethyl)benzoic acid → 3-Amino-5-(trifluoromethyl)benzoic acid

HRID 2075065Notes

Reaction equation

HRID 2075065 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:12]=1)[C:7]([OH:9])=[O:8])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:10]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:12]=1)[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 6166023-Nitro-5-(trifluoromethyl)benzoic acid

Product 1

HCID 6095563-Amino-5-(trifluoromethyl)benzoic acidYield 92.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 3-nitro-5-(trifluoromethyl)benzoic acid (9.8 gm, 41.7 mmol) in methanol (100 mL) was added 10% palladium on carbon (50% water content, 1.5 gm) and the suspension was shaken in a Parr® hydrogenation apparatus (Parr Instrument Company, Moline, Ill.) under a hydrogen atmosphere (40 psi). After 2 hours the catalyst was removed by filtration through a pad of celite, the pad rinsed through with methanol and the solvent evaporated under reduced pressure to give the title compound as a yellow solid (7.90 gm, 92%).

Workup

  1. customAfter 2 hours the catalyst was removed by filtration through a pad of celite
  2. washthe pad rinsed through with methanol
  3. customthe solvent evaporated under reduced pressure

Sources & evidence

ORD record
ord-11a0f3b0d1944d8685ca6336cb8cd604
Source dataset
uspto-grants-2011_04
Patent number
US07919506B2

Reaction notes

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