Acetic Anhydride → N-Acetyl-3-nitrobenzamide

HRID 1588030Notes

Reaction equation

HRID 1588030 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH2:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[C:13](OC(=O)C)(=[O:15])[CH3:14]>C(Cl)Cl>[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([NH:12][C:13](=[O:15])[CH3:14])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 7918Acetic Anhydride2×HCID 125763-Nitrobenzamide

Product 1

HCID 19756873N-Acetyl-3-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-nitrophenylcarboxamide (2 g) in 125 ml of dry methylene chloride was cooled to 0° C. and mixed with 1.25 ml of acetic anhydride and 2.1 g of 4-N,N-dimethylaminopyridine. The reaction mixture was warmed to room temperature and stirred for 1 hour. Additional amounts of 4-N,N-dimethylaminopyridine (809 mg) and acetic anhydride (1.25 ml) were added to the reaction mixture and stirring was continued overnight. The reaction mixture was diluted with 300 ml of methylene chloride and was washed with 60 ml of 5% citric acid solution. The organic extracts were dried, concentrated in vacuo, and the residue was chromatographed on silica gel (chloroform-methanol, 97:3 v/v) to yield 500 mg of the title compound in pure form.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. washwas washed with 60 ml of 5% citric acid solution
  4. customThe organic extracts were dried
  5. concentrationconcentrated in vacuo
  6. customthe residue was chromatographed on silica gel (chloroform-methanol, 97:3 v/v)

Sources & evidence

ORD record
ord-e3bf2dacc70641d8a5b5e65fc9e17504
Source dataset
uspto-grants-1993_06
Patent number
US05220018

Reaction notes

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