Acetic Anhydride → N-(4-Chloro-3-hydroxyphenyl)acetamide

HRID 330782

Reaction equation

HRID 330782 reaction equation
C(O[C:5](=[O:7])[CH3:6])(=O)C.[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH2:13])=[CH:11][C:10]=1[OH:16]>C(O)(=O)C>[Cl:8][C:9]1[CH:15]=[CH:14][C:12]([NH:13][C:5](=[O:7])[CH3:6])=[CH:11][C:10]=1[OH:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 806765-Amino-2-chlorophenol

Product 1

HCID 14122483N-(4-Chloro-3-hydroxyphenyl)acetamideYield 93%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Acetic anhydride (3.0 mL, 42.0 mmol) was added to a solution of 4-chloro-3-hydroxy aniline (4.0 g, 28 mmol) in acetic acid (20 mL), and the reaction was refluxed for 5 mins. The reaction mixture was cooled to room temperature and the product was solidified. It was filtered off and washed with water (10 mL) and dried to obtain the product 17a in 93% yield (4.8 g) as a creamy white solid. There was no need for further purification.

Workup

  1. temperaturethe reaction was refluxed for 5 mins
  2. filtrationIt was filtered off
  3. washwashed with water (10 mL)
  4. customdried

Sources & evidence

ORD record
ord-b36c980b138d4933833e7cd7a8fdd153
Source dataset
uspto-grants-2014_11
Patent number
US08877752B2

Linked notes

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