C,C,C-trifluoro-N-(3-nitro-phenyl)-methanesulfonamide → N-(3-Amino-phenyl)-C,C,C-trifluoro-methanesulfonamide

HRID 537871

Reaction equation

HRID 537871 reaction equation
[F:1][C:2]([F:17])([F:16])[S:3]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([N+:13]([O-])=O)[CH:8]=1)(=[O:5])=[O:4]>C(O)C.[Pd]>[NH2:13][C:9]1[CH:8]=[C:7]([NH:6][S:3]([C:2]([F:17])([F:1])[F:16])(=[O:5])=[O:4])[CH:12]=[CH:11][CH:10]=1

Participants

4

Reactant 1

HCID 69148322C,C,C-trifluoro-N-(3-nitro-phenyl)-methanesulfonamide

Product 1

HCID 21757535N-(3-Amino-phenyl)-C,C,C-trifluoro-methanesulfonamideYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

1,1,1-trifluoro-N-(3-nitrophenyl)methanesulfonamide 42 (0.5 g, 1.85 mmol) was dissolved in ethanol (20 mL) treated with H2 (30 psi, Parr hydrogenator) for 2 h in the presence of Pd/C (catalytic, 50 mg). The reaction was monitored by TLC until the starting material was no longer detected. The Pd/C residue was removed by filtration over celite pad, followed by rotary evaporation of the solvent obtained 0.44 g of N-(3-aminophenyl)-1,1,1-trifluoromethanesulfonamide 43 (100% yield). The crude product was further used without further purification. MS (ES) m/z 241 (M+H+).

Workup

  1. customThe Pd/C residue was removed by filtration over celite pad
  2. customfollowed by rotary evaporation of the solvent

Sources & evidence

ORD record
ord-1a2997a9f5e34a278c87c3d04c34da24
Source dataset
uspto-grants-2014_10
Patent number
US08865709B2

Linked notes

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