Acetic Anhydride → N-(2-Acetylphenyl)acetamide

HRID 990109

Reaction equation

HRID 990109 reaction equation
[C:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH2:6])(=[O:3])[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[C:17](OC(=O)C)(=[O:19])[CH3:18]>>[C:1]([C:4]1[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=1[NH:6][C:17](=[O:19])[CH3:18])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 10340Sodium CarbonateHCID 110862'-Aminoacetophenone

Product 1

HCID 21306N-(2-Acetylphenyl)acetamide

Procedure

A mixture of 2-acetylaniline (1 ml; 8.3 mmol) and acetic anhydride (10 ml) was stirred overnight at ambient temperature. Saturated aqueous sodium carbonate was added till basic reaction and the resulting mixture was extracted with ethyl acetate. The organic phase was dried over sodium sulphate and evaporated under reduced pressure to leave N-(2-acetylphenyl)acetamide quantitatively. This product was dissolved in ethanol (40 ml) and hydroxylamine, hydrochloride (0.94 g; 13.6 mmol) was added. The mixture was heated to reflux for 7 hours and then left at ambient temperature overnight. The solvent was removed by evaporation and the residue was partitioned between ethyl acetate and aqueous sodium carbonate. The organic phase was concentrated and subjected to chromatography on silica gel using a mixture of ethyl acetate and methanol (9:1 v/v) as the eluent. Yield: 0.26 g (15%). Mp. 99-100° C.

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulphate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-7df4440d40f443179961745c6ae01220
Source dataset
uspto-grants-2002_10
Patent number
US06458846B1

Linked notes

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