2-Nitro-4-(trifluoromethyl)benzoic acid → 4-(Trifluoromethyl)anthranilic acid

HRID 2289577Notes

Reaction equation

HRID 2289577 reaction equation
[F:1][C:2]([F:16])([F:15])[C:3]1[CH:11]=[CH:10][C:6]([C:7]([OH:9])=[O:8])=[C:5]([N+:12]([O-])=O)[CH:4]=1>CO.[Pd]>[NH2:12][C:5]1[CH:4]=[C:3]([C:2]([F:1])([F:15])[F:16])[CH:11]=[CH:10][C:6]=1[C:7]([OH:9])=[O:8]

Participants

4

Reactant 1

HCID 6420962-Nitro-4-(trifluoromethyl)benzoic acid

Product 1

HCID 678694-(Trifluoromethyl)anthranilic acidYield 100.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 4-trifluoromethyl-2-nitrobenzoic acid (5.23 g, 22.2 mmol) in methanol (200 ml) was added 10% palladium on carbon (500 mg). The mixture was stirred under a hydrogen atmosphere for 35 min. The reaction mixture was filtered through Celite, and the solvent was removed under reduced pressure to give 2-amino-4-trifluoromethylbenzoic acid (4.57 g, 100%).

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-55f371537d7e4d5c86911c2c5c766fda
Source dataset
uspto-grants-2000_07
Patent number
US06093714

Reaction notes

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