4-Nitro-2-(trifluoromethyl)anisole → 5-Amino-2-methoxybenzotrifluoride

HRID 1269842Notes

Reaction equation

HRID 1269842 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][C:4]=1[C:12]([F:15])([F:14])[F:13]>CO.[Pd]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][C:4]=1[C:12]([F:13])([F:14])[F:15]

Participants

4

Reactant 1

HCID 695624-Nitro-2-(trifluoromethyl)anisole

Product 1

HCID 6007055-Amino-2-methoxybenzotrifluorideYield 106.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of 2-methoxy-5-nitrobenzotrifluoride (5.08 g, 23.0 mmol) in methanol (200 ml) was added 10% Pd—C (containing 50% water, 250 mg), and the resulting mixture was stirred for 3.5 hours under a hydrogen atmosphere at room temperature and atmospheric pressure while maintaining the temperature. The mixture was filtered by the use of Celite and the filtrate was concentrated to dryness under reduced pressure to obtain 4-methoxy-3-(trifluoromethyl)aniline (4.67 g, 100%).

Workup

  1. temperatureatmospheric pressure while maintaining the temperature
  2. filtrationThe mixture was filtered by the use of Celite
  3. concentrationthe filtrate was concentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-97c7250a2f9e42f0919bba9ef7816f49
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…