(3-Nitro-5-(trifluoromethyl)phenyl)methanol → (3-Amino-5-(trifluoromethyl)phenyl)methanol

HRID 391377

Reaction equation

HRID 391377 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:9]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:14][OH:15])[CH:7]=[C:8]([C:10]([F:11])([F:12])[F:13])[CH:9]=1

Participants

4

Reactant 1

HCID 18621888(3-Nitro-5-(trifluoromethyl)phenyl)methanol

Product 1

HCID 53414333(3-Amino-5-(trifluoromethyl)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(3-Nitro-5-(trifluoromethyl)phenyl)methanol (2.6 g, 11.6 mmol) in methanol (30 mL) was flushed with nitrogen, and treated with palladium (10% on charcoal, 260 mg). The flask was flushed with hydrogen and allowed to stir under an atmosphere of hydrogen overnight. The reaction was flushed with nitrogen, filtered through celite, and concentrated. Column chromatography on silica gel (50% ethyl acetate/hexanes) afforded 1.9 g (85%). 1H-NMR (CDCl3, 500 MHz) δ 6.95 (s, 1H), 6.80 (s, 1H), 6.79 (s, 1H), 4.61 (s, 2H). Mass spec.: 192.15 (MH)+.

Workup

  1. customThe flask was flushed with hydrogen
  2. customThe reaction was flushed with nitrogen
  3. filtrationfiltered through celite
  4. concentrationconcentrated
  5. customColumn chromatography on silica gel (50% ethyl acetate/hexanes) afforded 1.9 g (85%)

Sources & evidence

ORD record
ord-c5431651436b4c4ba551a8949bf0c2a6
Source dataset
uspto-grants-2013_02
Patent number
US08383821B2

Linked notes

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