3-Hydroxy-5-nitrobenzotrifluoride → 3-aMino-5-(trifluoroMethyl)phenol

HRID 1846252Notes

Reaction equation

HRID 1846252 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O.[H][H]>CO.[Ni]>[NH2:1][C:4]1[CH:5]=[C:6]([OH:14])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

5

Reactant 2

HCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 178418361HCID 178418361, compound

Product 1

HCID 144012293-aMino-5-(trifluoroMethyl)phenolYield 98.2%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-nitro-5-(trifluoromethyl)phenol (50 g, 241.42 mmol, 1.00 equiv) and Raney-Ni (6 g) in methanol (500 mL) was stirred under 1 atmosphere of hydrogen at 25° C. for 8 h. The catalyst was removed by filtration. The filtrate was concentrated under vacuum to give 42 g (98%) of 3-amino-5-(trifluoromethyl)phenol as a light yellow solid. LCMS (method D, ESI): RT=0.84 min, m/z=178.0 [M+H]+.

Workup

  1. customThe catalyst was removed by filtration
  2. concentrationThe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-f448b48128634c84bd77b7360b9887d7
Source dataset
uspto-grants-2015_02
Patent number
US08952026B2

Reaction notes

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