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

HRID 18939Notes

Reaction equation

HRID 18939 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:12]=[C:11]([C:13]([F:14])([F:15])[F:16])[CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=[O:7]

Participants

4

Reactant 1

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

Product 1

HCID 678694-(Trifluoromethyl)anthranilic acidYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a 100 mL flask containing 2-nitro-4-(trifluoromethyl)benzoic acid (940.5 mg, 4 mmol) in 30 mL MeOH was added 100 mg of 10% Pd on charcoal After flushing with hydrogen three times, the reaction mixture was agitated under hydrogen atmosphere for 2 h. The mixture was filtered through a plug of Celite, and the filtrate was concentrated to afford 2-amino-4-(trifluoromethyl)benzoic acid (740 mg, 3.6 mmol, 90%).

Workup

  1. customAfter flushing with hydrogen three times
  2. filtrationThe mixture was filtered through a plug of Celite
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-51ea03174d514bc590070b56295230a0
Source dataset
uspto-grants-2010_06
Patent number
US07741479B2

Reaction notes

Loading…