2-Nitro-6-(trifluoromethyl)phenol → 2-Amino-6-(trifluoromethyl)phenol

HRID 641585Notes

Reaction equation

HRID 641585 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:13])([F:12])[F:11])[C:5]=1[OH:14])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([C:10]([F:11])([F:12])[F:13])[C:5]=1[OH:14]

Participants

4

Reactant 1

HCID 9018342-Nitro-6-(trifluoromethyl)phenol

Product 1

HCID 222727462-Amino-6-(trifluoromethyl)phenolYield 71.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Nitro-6-trifluoromethyl-phenol (1.8 g) (J. Org. Chem. 1962, 27, 4660-4662) was dissolved in MeOH (20 ml) prior to the addition of 10% Pd/C (1.0 g). The reaction was placed on a Parr aparatus under hydrogen at 60 psi for 4 h. The palladium was filtered off and the solution was concentrated to give 2-amino-6-trifluoromethyl-phenol (1.1 g): 1H NMR (CD3OD, δ ppm, 300 mHz) 6.78 (m, 2H), 6.90 (d, 1H).

Workup

  1. filtrationThe palladium was filtered off
  2. concentrationthe solution was concentrated

Sources & evidence

ORD record
ord-fdc98fecf2c843858f30dc2bb32b91e2
Source dataset
uspto-grants-2010_04
Patent number
US07696205B2

Reaction notes

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