Acetic Anhydride → N-(2-Acetylphenyl)acetamide

HRID 1251292Notes

Reaction equation

HRID 1251292 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[O:10])[CH3:9].[C:11](OC(=O)C)(=[O:13])[CH3:12]>>[C:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[NH:1][C:11](=[O:13])[CH3:12])(=[O:10])[CH3:9]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 110862'-Aminoacetophenone

Product 1

HCID 21306N-(2-Acetylphenyl)acetamideYield 88.2%

Conditions

Temperature
4 °C

Procedure

To 1-(2-amino-phenyl)-ethanone 2 (90.37 g, 0.67 moles) was added acetic anhydride (68.25 g, 0.67 moles) and stirred for 2 h at 4° C. The reaction mixture was poured into crushed ice and the precipitate was filtered, washed with ice water, and air-dried to afford N-(2-acetyl-phenyl)-acetamide 3 (104.70 g, 88% yield). 1HNMR (400 MHz, DMSO-d6) δ2.10 (s, 3H), 2.60 (s, 3H), 7.17-7.21 (m, 1H), 7.55-7.59 (m, 1H), 7.95 (d, 1H, J=8.0 Hz), 8.26 (d, 1H, J=8.0 Hz), 11.16 (s 1H); MS m/z 17 (M+).

Workup

  1. additionThe reaction mixture was poured
  2. custominto crushed ice
  3. filtrationthe precipitate was filtered
  4. washwashed with ice water
  5. customair-dried

Sources & evidence

ORD record
ord-f4c62a53faa44f80af80e4fd3c3c9c9d
Source dataset
uspto-grants-2002_01
Patent number
US06342079B1

Reaction notes

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