Acetic Anhydride → N-(4-Methyl-3-nitrophenyl)acetamide

HRID 53290

Reaction equation

HRID 53290 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10].[C:12](OC(=O)C)(=[O:14])[CH3:13]>>[CH3:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12](=[O:14])[CH3:13])=[CH:4][C:3]=1[N+:9]([O-:11])=[O:10]

Participants

3

Reactant 2

HCID 7918Acetic AnhydrideHCID 83904-Methyl-3-nitroaniline

Product 1

HCID 73133N-(4-Methyl-3-nitrophenyl)acetamide

Procedure

A solution of 4-methyl-3-nitroaniline (3.60 g, 23.7 mmol) in acetic anhydride (28 mL) was allowed to stir at room temperature. After 16 h, the reaction mixture was concentrated in vacuo, diluted with ethyl acetate (25 mL), washed with saturated sodium bicarbonate (2×50 mL), dried over anhydrous sodium sulfate and concentrated in vacuo to give 4.20 g (Y: 99%) of the title compound; 1H-NMR (CDCl3): δ8.10 (d, J=1.7 Hz, 1H), 7.75 (dd, J=8.5, 1.7 Hz, 1H), 7.38 (bs, 1H), 7.29 (d, J=8.5 Hz, 1H), 2.56 (s, 3H), 2.21 (s, 3H); MS (DCI) m/e: 195 (MH+).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. additiondiluted with ethyl acetate (25 mL)
  3. washwashed with saturated sodium bicarbonate (2×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cdfad0d4ad1b4ee185df1f48c3fd8b0b
Source dataset
uspto-grants-1997_04
Patent number
US05618839

Linked notes

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