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

HRID 369103Notes

Reaction equation

HRID 369103 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-])=O)=[C:6]([OH:8])[CH:7]=1>[Pd].C(O)C>[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 87%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To 50 ml of ethanol was added 5-fluoro-2-nitrophenol (7.86 g, 50 mmol) and 10% Pd/C (0.786 g) and the mixture was stirred under a hydrogen stream for 3 hours at room temperature. Then the reaction mixture was filtered and the filtrate concentrated. The residue was subjected to recrystallization from toluene to afford 2-amino-5-fluoro-phenol (5.52 g, yield: 87%).

Workup

  1. filtrationThen the reaction mixture was filtered
  2. concentrationthe filtrate concentrated
  3. customThe residue was subjected to recrystallization from toluene

Sources & evidence

ORD record
ord-edf1552a61b64bd29e27b1feb17c3615
Source dataset
uspto-grants-2000_10
Patent number
US06136831

Reaction notes

Loading…