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

HRID 906499Notes

Reaction equation

HRID 906499 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 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-nitro-4-trifluoromethyl-benzoic acid (100 g, 425 mmol) in MeOH (600 mL) was treated with palladium on carbon (10%) and the mixture was stirred at r.t. for 2 h under hydrogen (7 bars). The mixture was then filtered and concentrated in vacuo to give 2-amino-4-trifluoromethyl-benzoic acid (87.2 g, 425 mmol, 100%) as a yellow solid, m.p. 172-173° C., ESI-MS: m/z 206 [M+H]+.

Workup

  1. filtrationThe mixture was then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-93b8c066291c4ce2b57590487b3d2b49
Source dataset
uspto-grants-2011_09
Patent number
US08012988B2

Reaction notes

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