5-Fluoro-2-nitrophenol → 2-Amino-5-fluorophenol

HRID 1184332Notes

Reaction equation

HRID 1184332 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1>C(O)C.[Pd]>[NH2:9][C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][C:6]=1[OH:8]

Participants

4

Reactant 1

HCID 99375-Fluoro-2-nitrophenol

Product 1

HCID 1857632-Amino-5-fluorophenolYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 5-fluoro-2-nitrophenol (26.63 g, 170 mmol) in ethanol under N2 atmosphere was added palladium on carbon (10 wt %, 250 mg, 0.235 mmol). The mixture was flushed with H2 and stirred at RT under H2 (balloon) until complete conversion according to thin layer chromatography (TLC) analysis. Pd/C was removed by filtration and the filtrate was concentrated to yield 21.6 g of the title compound.

Workup

  1. customThe mixture was flushed with H2
  2. customPd/C was removed by filtration
  3. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-f62a85dfe9894bde9fa9edbffaf0a245
Source dataset
uspto-grants-2014_03
Patent number
US08669208B2

Reaction notes

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