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

HRID 2122010

Reaction equation

HRID 2122010 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 96.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 4-chloro-3-nitroaniline (17.3 g, 100 mmol) in DCM (150 mL) was added dropwise acetic anhydride (14 mL, 150 mmol) at ambient temperature. The mixture was stirred at ambient temperature for 2.5 h. The solvent was removed in vacuo, and Et2O was added to the residue. The precipitate was collected by filtration, washed with Et2O, and dried in vacuo to give N-(4-chloro-3-nitrophenyl)acetamide (20.7 g, 96%), which was used without further purification.

Workup

  1. customThe solvent was removed in vacuo, and Et2O
  2. additionwas added to the residue
  3. filtrationThe precipitate was collected by filtration
  4. washwashed with Et2O
  5. customdried in vacuo

Sources & evidence

ORD record
ord-92b72ee7c9184a7282a64c27b1157a3c
Source dataset
uspto-grants-2004_02
Patent number
US06696473B2

Linked notes

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