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

HRID 1672177Notes

Reaction equation

HRID 1672177 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.C(Cl)Cl.CO>[Pd].CO>[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

5

Reactant 2

HCID 6420962-Nitro-4-(trifluoromethyl)benzoic acidHCID 21226129Dichloromethane methanol

Product 1

HCID 678694-(Trifluoromethyl)anthranilic acidYield 92.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 2-nitro-4-(trifluoromethyl)benzoic acid (646 g, 2.75 mol) and 10% palladium on carbon (50% in water, 71 g) in MeOH (3.6 L) was allowed to stir at rt under an atmosphere of H2 (15 psi). After 3 h, TLC (DCM:MeOH 10:1) showed no remaining starting material. The mixture was filtered and the filtrate was concentrated to give 2-amino-4-(trifluoromethyl)benzoic acid (520 g, 92%) as a white solid.

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-28f872740f67411da6fb38bfe589451d
Source dataset
uspto-grants-2011_08
Patent number
US07998952B2

Reaction notes

Loading…