4-Fluoro-2-nitrophenol → 2-Amino-4-fluorophenol

HRID 1533880Notes

Reaction equation

HRID 1533880 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1>C(O)C.[Pt]=O>[NH2:9][C:4]1[CH:3]=[C:2]([F:1])[CH:7]=[CH:6][C:5]=1[OH:8]

Participants

4

Reactant 1

HCID 1362364-Fluoro-2-nitrophenol

Product 1

HCID 27359172-Amino-4-fluorophenolYield 106.2%

Reagents, catalysts & solvents 2

HCID 82844Platinum oxide (PtO)CatalystHCID 702EthanolSolvent

Procedure

To a solution of 4-fluoro-2-nitrophenol (48.3 g, 0.30 mole) in 300 ml ethanol was added 0.24 g platinum oxide under nitrogen atmosphere. The mixture was hydrogenated with a Parr shaker for 8 hours at 45 psi. The catalyst was filtered off and the filtrate was concentrated to leave 40.5 g of the title compound as a brown powder. The NMR spectrum showed absorption at 4.79 (br.s, 2H), 6.11 (m, 1H), 6.36 (dd, 1H, J=11, 3 Hz), 6.53 (dd, 1H, J=5, 9 Hz) and 8.89 (s, 1H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-4291bf503c3f48aaa91367422790dd24
Source dataset
uspto-grants-1992_02
Patent number
US05086062

Reaction notes

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