2-Nitro-4-(trifluoromethyl)phenol → 2-Amino-4-(trifluoromethyl)phenol

HRID 1772283Notes

Reaction equation

HRID 1772283 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[CH:6][C:5]=1[OH:14])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:7]=[CH:6][C:5]=1[OH:14]

Participants

4

Reactant 1

HCID 98162-Nitro-4-(trifluoromethyl)phenol

Product 1

HCID 1202462-Amino-4-(trifluoromethyl)phenolYield 102.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2-Nitro-4-trifluoromethylphenol (340 μL, 2.41 mmol) was dissolved in methanol (50 mL) and processed through the H-Cube with a 10% Pd/C Catalyst cartridge at ambient temperature and pressure. The eluent was concentrated under reduced pressure to provide 2-amino-4-trifluoromethylphenol as a light brown solid (438 mg, 100%). (CI, m/z): [M+H]+ 178, [M−H]− 176; 1H NMR (CDCl3): δ 6.96 (d, J=2.0 Hz, 1H), 6.89-6.94 (m, 1H), 6.74 (d, J=8.2 Hz, 1H), 4.10 (br s, 2H).

Workup

  1. concentrationThe eluent was concentrated under reduced pressure

Sources & evidence

ORD record
ord-a5cddc1e2c12412e916de87aa6e49bab
Source dataset
uspto-grants-2016_02
Patent number
US09249102B2

Reaction notes

Loading…