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

HRID 971075Notes

Reaction equation

HRID 971075 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH2:16])=[CH:12][CH:11]=1.CCCCCC>ClCCl>[CH3:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:1](=[O:3])[CH3:2])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 7918Acetic AnhydrideHCID 8058Hexane

Product 1

HCID 5827N-(4-Methoxyphenyl)AcetamideYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (10.21 g, 9.4 mL, 100 mmol) was added dropwise over 1 hour to a stirred solution of p-anisidine (12.32 g, 100 mmol) in dichloromethane (40 mL) at 25-30° C. The mixture was stirred for an additional 1 hour at the same temperature. Hexane (120 mL) was added dropwise to the mixture at 25-30° C. The obtained suspension was stirred for 1 hour at the same temperature. The precipitated crystals were separated by filtration and dried under reduced pressure to give 15.31 g (92.7%) of N-(4-methoxyphenyl)acetamide [3a] as off-white crystals.

Workup

  1. stirringThe obtained suspension was stirred for 1 hour at the same temperature
  2. customThe precipitated crystals were separated by filtration
  3. customdried under reduced pressure

Sources & evidence

ORD record
ord-38322b5735724350b04435a1314156df
Source dataset
uspto-grants-2007_12
Patent number
US07312345B2

Reaction notes

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