N-Benzoyl-3-(trifluoromethyl)-4-nitroaniline → N-[4-amino-3-(trifluoromethyl)phenyl]benzamide

HRID 2233232Notes

Reaction equation

HRID 2233232 reaction equation
[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-])=O)=[C:12]([C:19]([F:22])([F:21])[F:20])[CH:11]=1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[Pt](=O)=O>[C:1]([NH:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[C:12]([C:19]([F:20])([F:21])[F:22])[CH:11]=1)(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 44203033N-Benzoyl-3-(trifluoromethyl)-4-nitroaniline

Product 1

HCID 16772080N-[4-amino-3-(trifluoromethyl)phenyl]benzamideYield 91%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

Platinum dioxide (100 mg, 0.44 mmol) was added to a solution of N-benzoyl 3-(trifluoromethyl)-4-nitroaniline (913 mg, 2.94 mmol) in ethanol (50 ml) at ambient temperature and the reaction stirred for 1.5 hours under an atmosphere of hydrogen. Filtration of the reaction through a pad of celite and solvent evaporation in vacuo, yielded N-benzoyl 3-(trifluoromethyl)-4-aminoaniline (750 mg, 91% yield) as an off-white solid:

Workup

  1. filtrationFiltration of the reaction
  2. customthrough a pad of celite and solvent evaporation in vacuo

Sources & evidence

ORD record
ord-6640c2581dca4f0fb5b913abb099c106
Source dataset
uspto-grants-2010_05
Patent number
US07709479B1

Reaction notes

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