3-Chloro-2-methylaniline → N-(3-chloro-2-methylphenyl)acetamide

HRID 2102024

Reaction equation

HRID 2102024 reaction equation
[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[C:10](OC(=O)C)(=[O:12])[CH3:11]>CCO>[Cl:1][C:2]1[C:3]([CH3:9])=[C:4]([NH:5][C:10](=[O:12])[CH3:11])[CH:6]=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 68943-Chloro-2-methylanilineHCID 7918Acetic Anhydride

Product 1

HCID 81969N-(3-chloro-2-methylphenyl)acetamideYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 3-chloro-2-methylaniline (9.0 g, 63.56 mmol) in EtOH (75 mL) was treated with acetic anhydride (7.2 mL, 76.31 mmol) and the resulting mixture was stirred at rt for 3 h. Concentration was followed by crystallization from hexanes/EtOAc (1:3) to afford 11.2 g of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 9.52 (s, 1H), 7.30-7.23 (m, 2H), 7.17-7.13 (m, 1H), 2.18 (s, 3H), 2.06 (s, 3H).

Workup

  1. concentrationConcentration
  2. customwas followed by crystallization from hexanes/EtOAc (1:3)

Sources & evidence

ORD record
ord-5fd8a561f3a24ccd91e18344ba9e5335
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Linked notes

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