4-Nitro-3-trifluoromethylphenol → 2-Amino-5-hydroxybenzotrifluoride

HRID 2374048Notes

Reaction equation

HRID 2374048 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:14])([F:13])[F:12])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:5]=1[C:11]([F:12])([F:13])[F:14]

Participants

4

Reactant 1

HCID 69314-Nitro-3-trifluoromethylphenol

Product 1

HCID 146928342-Amino-5-hydroxybenzotrifluorideYield 98.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-nitro-3-(trifluoromethyl)phenol (Aldrich, 414 mg, 2.0 mmol) in 10 mL of MeOH was added 10% Pd/C (100 mg). The suspension was stirred under H2 atmosphere for 12 h and it was then filtered and concentrated in vacuo to give 4-amino-3-(trifluoromethyl)phenol (350 mg, 95% yield), which was sufficiently pure to use in the next step. MS(ESI+): m/z 178.02 (M+H)+.

Workup

  1. filtrationit was then filtered
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-40223d8e22024fa59dabe0188ba998da
Source dataset
uspto-grants-2008_12
Patent number
US07459562B2

Reaction notes

Loading…