2-Chloro-5-nitrophenol → 5-Amino-2-chlorophenol

HRID 8630

Reaction equation

HRID 8630 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[OH:11]>C(OCC)(=O)C.[Pt]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH2:8])=[CH:4][C:3]=1[OH:11]

Participants

4

Reactant 1

HCID 692642-Chloro-5-nitrophenol

Product 1

HCID 806765-Amino-2-chlorophenol

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-5-nitrophenol (114 g, 0.66 mol) in ethyl acetate (500 mL) was treated with 5% Pt/C (510 mg, 0.5 weight %) and the mixture shaken under a hydrogen atmosphere (30 psi) for 6 h. The mixture was filtered through Celite® and the residue washed well with ethyl acetate. Evaporation of the ethyl acetate gave a solid (95 g, 100% crude yield) which was taken directly into the next step.

Workup

  1. filtrationThe mixture was filtered through Celite®
  2. washthe residue washed well with ethyl acetate
  3. customEvaporation of the ethyl acetate
  4. customgave a solid (95 g, 100% crude yield) which

Sources & evidence

ORD record
ord-03a6ba3e17a44728844857814bf2bd02
Source dataset
uspto-grants-2006_08
Patent number
US07091204B2

Linked notes

Loading…