4-Chloro-3-nitrophenol → 3-Amino-4-chlorophenol

HRID 481349Notes

Reaction equation

HRID 481349 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[N+:9]([O-])=O>CO.[Pd]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][C:3]=1[NH2:9]

Participants

4

Reactant 1

HCID 691274-Chloro-3-nitrophenol

Product 1

HCID 50700783-Amino-4-chlorophenol

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 4-chloro-3-nitrophenol (2.67 g, 15.4 mmol) in methanol (30 ml) is stirred for 24 h under a hydrogen atmosphere in the presence of a catalytic amount of Pd/C. After this time, the reaction mixture is filtered through Celite and then concentrated. It is purified by flash chromatography with a mixture (95/5/1) and then (90/9/1) of dichloromethane/methanol/aqueous ammonia.

Workup

  1. filtrationAfter this time, the reaction mixture is filtered through Celite
  2. concentrationconcentrated
  3. customIt is purified by flash chromatography with a mixture (95/5/1)

Sources & evidence

ORD record
ord-35fe57949b3e4ab1bfe256fb6737b1b9
Source dataset
uspto-grants-1998_08
Patent number
US05789412

Reaction notes

Loading…