Acetic Anhydride → N-(4-Chloro-2-hydroxyphenyl)acetamide

HRID 270073

Reaction equation

HRID 270073 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([Cl:8])=[CH:4][C:3]=1[OH:9].[C:10](OC(=O)C)(=[O:12])[CH3:11]>CO>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]([NH:1][C:10](=[O:12])[CH3:11])=[C:3]([OH:9])[CH:4]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 915912-Amino-5-chlorophenol

Product 1

HCID 177739N-(4-Chloro-2-hydroxyphenyl)acetamideYield 91.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 2-amino-5-chlorophenol (1.01 g, 7.0 mmol) in methanol (10 mL) was added acetic anhydride (1.08 g, 10.55 mmol) and the reaction mixture was stirred at room temperature for 30 min. The volatiles were removed in vacuo and the residue was purified by silica gel flash chromatography (hexane:ethyl acetate 5:2) to give the subtitled compound (1.19 g).

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residue was purified by silica gel flash chromatography (hexane:ethyl acetate 5:2)

Sources & evidence

ORD record
ord-c24fa62b13a64ab6b70ce5338142fb9d
Source dataset
uspto-grants-2008_11
Patent number
US07449475B2

Linked notes

Loading…