Water → N-(3,5-dimethoxyphenyl)acetamide

HRID 1178299Notes

Reaction equation

HRID 1178299 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([O:10][CH3:11])[CH:9]=1)[NH2:6].[C:12](OC(=O)C)(=[O:14])[CH3:13].O>N1C=CC=CC=1.C([O-])([O-])=O.[Na+].[Na+]>[CH3:11][O:10][C:8]1[CH:7]=[C:5]([NH:6][C:12](=[O:14])[CH3:13])[CH:4]=[C:3]([O:2][CH3:1])[CH:9]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 663013,5-Dimethoxyaniline

Product 1

HCID 702039N-(3,5-dimethoxyphenyl)acetamide

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 10340Sodium CarbonateSolvent

Procedure

A solution of 15.3 g of 3,5-dimethoxyaniline and 57.5 ml of acetic anhydride in 40 ml of anhydrous pyridine is heated at reflux for 1 hour. The reaction mixture is then cooled and poured into 350 ml of water. The precipitate formed is suspended in 20% aqueous Na2CO3 solution and is then filtered off using a Buchner funnel, washed with water and dried under a phosphoric vacuum. A precipitate of 14.5 g of the expected product is obtained in the form of a white amorphous solid.

Workup

  1. temperatureat reflux for 1 hour
  2. temperatureThe reaction mixture is then cooled
  3. customThe precipitate formed
  4. filtrationis then filtered off
  5. washwashed with water
  6. customdried under a phosphoric vacuum

Sources & evidence

ORD record
ord-462c7f7e57814880844ee9c620f48b28
Source dataset
uspto-grants-2007_10
Patent number
US07276512B2

Reaction notes

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