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

HRID 2237268Notes

Reaction equation

HRID 2237268 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-0189b3ba0b6249f5bca4f01c696d3187
Source dataset
uspto-grants-2010_05
Patent number
US07714138B2

Reaction notes

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