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

HRID 1042443Notes

Reaction equation

HRID 1042443 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>[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

3

Reactant 1

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

Product 1

HCID 678694-(Trifluoromethyl)anthranilic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

2-Nitro-4-trifluoromethyl-benzoic acid (3.07 g, 13.0 mmol) was stirred with Pd/C under hydrogen atmosphere for 2 hrs. The reaction mixture was filtered with celite to remove Pd/C. The filterate was concentrated in vacuo. The residue was extracted with CH2Cl2 (30 ml×3) and H2O (30 ml). The combined organic layer was dried over MgSO4 and then concentrated to yield title compound (2.66 g, 99%).

Workup

  1. filtrationThe reaction mixture was filtered with celite
  2. customto remove Pd/C
  3. concentrationThe filterate was concentrated in vacuo
  4. extractionThe residue was extracted with CH2Cl2 (30 ml×3) and H2O (30 ml)
  5. dry with materialThe combined organic layer was dried over MgSO4
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-16ea46513a504758a99105cb26a2fbac
Source dataset
uspto-grants-2013_10
Patent number
US08557872B2

Reaction notes

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