P-Anisidine → N-(4-Methoxyphenyl)Acetamide

HRID 1819552Notes

Reaction equation

HRID 1819552 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1.[C:10](OC(=O)C)(=[O:12])[CH3:11]>ClCCl>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10](=[O:12])[CH3:11])=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 7732P-AnisidineHCID 7918Acetic Anhydride

Product 1

HCID 5827N-(4-Methoxyphenyl)AcetamideYield 95.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring suspension of p-anisidine (6.036 g, 49 mmol) in dichloromethane (20 ml) was added acetic anhydride (5 ml, 53 mmol, 1.1 equ) over one hour. The reaction was stirred for a further hour then poured onto hexane (60 ml) and stirred for another hour. The solid was collected and washed with hexane to give N-(4-methoxy-phenyl)-acetamide 51 (7.717 g, 95%) as a pale grey solid.

Workup

  1. additionthen poured onto hexane (60 ml)
  2. stirringstirred for another hour
  3. customThe solid was collected
  4. washwashed with hexane

Sources & evidence

ORD record
ord-cfd0fd80d95f4cf894be048ac5ce01b8
Source dataset
uspto-grants-2009_10
Patent number
US07601754B2

Reaction notes

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