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

HRID 2122014Notes

Reaction equation

HRID 2122014 reaction equation
[Cl: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]>C(Cl)Cl>[Cl: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

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 124774-Chloro-3-nitroaniline

Product 1

HCID 79672N-(4-Chloro-3-nitrophenyl)acetamideYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-chloro-3-nitroaniline (51.8 g, 0.36 mol) in anhydrous DCM (300 mL) was added dropwise acetic anhydride (45 mL, 0.48 mol) at room temperature, and the resulting solution was stirred at room temperature for 3 h. The solvent was removed in vacuo, and Et2O was added to the residue. The precipitates were collected by filtration, washed thoroughly with Et2O, and dried under high vacuum to give 4′-chloro-3′-nitroacetanilide (78.7 g, 100%).

Workup

  1. customThe solvent was removed in vacuo, and Et2O
  2. additionwas added to the residue
  3. filtrationThe precipitates were collected by filtration
  4. washwashed thoroughly with Et2O
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-24d14610b97d416dba3a9ee226a36e56
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Reaction notes

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