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

HRID 1372667Notes

Reaction equation

HRID 1372667 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[C:4]([N+:9]([O-])=O)[CH:3]=1>CO.[C].[Pd]>[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 105%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

In methanol (20 ml) was dissolved 4-fluoro-2-nitrophenol (1.00 g, 6.37 mmol). To the resulting solution was added 10% palladium-carbon (0.20 g, 20 wt %). The resulting mixture was subjected to catalytic hydrogenation under stirring for 2 days. After the reaction mixture was filtered through Celite to remove the catalyst, the filtrate was distilled under reduced pressure to remove the solvent, whereby 2-amino-4-fluorophenol (850 mg, 100%) was obtained as a reddish brown solid.

Workup

  1. filtrationAfter the reaction mixture was filtered through Celite
  2. customto remove the catalyst
  3. distillationthe filtrate was distilled under reduced pressure
  4. customto remove the solvent

Sources & evidence

ORD record
ord-75dac2c756b745fcb48982b3e3794499
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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