2-Methyl-4-methoxyaniline → N-(4-Methoxy-2-methylphenyl)-acetamide

HRID 1661967Notes

Reaction equation

HRID 1661967 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH2:7])=[C:5]([CH3:10])[CH:4]=1.[C:11](OC(=O)C)(=[O:13])[CH3:12]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:6]([NH:7][C:11](=[O:13])[CH3:12])=[C:5]([CH3:10])[CH:4]=1

Participants

4

Reactant 2

HCID 76102-Methyl-4-methoxyanilineHCID 7918Acetic Anhydride

Product 1

HCID 95082N-(4-Methoxy-2-methylphenyl)-acetamideYield 82.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-methoxy-2-methylaniline (120 g, 0.88 mol) in DCM (400 mL) is added acetic acid anhydride (120 mL, 1.2 mol) dropwise. The reaction mixture is stirred at room temperature (RT) for 3 hours. After petroleum ether (PE) (1.6 L) is added, the slurry is stirred for another one hour. The precipitate is collected by filtration and is washed with PE to give the product as a pink solid (130 g, 82% yield). MS (m/z): 180.0 (M+H).

Workup

  1. stirringthe slurry is stirred for another one hour
  2. filtrationThe precipitate is collected by filtration
  3. washis washed with PE

Sources & evidence

ORD record
ord-0f7f470019c6433d90c419f299b64402
Source dataset
uspto-grants-2011_10
Patent number
US08030302B2

Reaction notes

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