2,2,2-trifluoro-N-(2-methyl-5-nitrophenyl)acetamide → N-(5-Amino-2-methyl-phenyl)-2,2,2-trifluoro-acetamide

HRID 1071524Notes

Reaction equation

HRID 1071524 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]([NH:5][C:6]1[CH:11]=[C:10]([N+:12]([O-])=O)[CH:9]=[CH:8][C:7]=1[CH3:15])=[O:4]>C(OCC)(=O)C>[NH2:12][C:10]1[CH:9]=[CH:8][C:7]([CH3:15])=[C:6]([NH:5][C:3](=[O:4])[C:2]([F:1])([F:16])[F:17])[CH:11]=1

Participants

3

Reactant 1

HCID 8307252,2,2-trifluoro-N-(2-methyl-5-nitrophenyl)acetamide

Product 1

HCID 22393536N-(5-Amino-2-methyl-phenyl)-2,2,2-trifluoro-acetamideYield 95%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

2,2,2-Trifluoro-N-(2-methyl-5-nitro-phenyl)-acetamide (3.91 g, 15.78 mmol) was taken up in ethyl acetate in a Paar vessel and flushed with argon. Palladium on carbon (400 mg) was added and the argon atmosphere was replaced with hydrogen at 50 psi. The vessel was shaken for 12 h. The hydrogen was then replaced with argon and the catalyst was removed by filtration through celite. The solvent was removed under reduced pressure to yield 3.27 g of the desired amine. C9H9F3N2O MS m/e=219.1 (M+H).

Workup

  1. customflushed with argon
  2. additionPalladium on carbon (400 mg) was added
  3. customthe catalyst was removed by filtration through celite
  4. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-79fc51b4576348d39ad160ac8c538be5
Source dataset
uspto-grants-2005_06
Patent number
US06906067B2

Reaction notes

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