Water → HCID 10631696, compound

HRID 326311Notes

Reaction equation

HRID 326311 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:6]=1[C:15](=[O:17])[CH3:16])(=O)C.[OH-].[K+].O>C(O)C>[NH2:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[C:6]=1[C:15](=[O:17])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 11345404HCID 11345404, compound2×

Product 1

HCID 10631696HCID 10631696, compoundYield 58.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (2'-acetylamino-4',6'-dimethoxyphenyl)ethanone (compound 75-3, prepared in Preparation 75) (0.237 g, 1.0 mmol), potassium hydroxide (0.2 g, 3.57 mmol), water (0.2 ml), and ethanol (2 ml) is heated to reflux for one hour. The solvent is distilled under reduced pressure, and the residue is extracted with dichloromethane. The extract is washed with water, dried, and the solvent is removed to yield a crystalline residue. Recrystallization from ethyl acetate gives (2'-amino-4',6'-dimethoxyphenyl)ethanone as a crystalline solid (0.114 g, 58%, m.p.=104°-105° C.).

Workup

  1. temperatureis heated
  2. temperatureto reflux for one hour
  3. distillationThe solvent is distilled under reduced pressure
  4. extractionthe residue is extracted with dichloromethane
  5. washThe extract is washed with water
  6. customdried
  7. customthe solvent is removed
  8. customto yield a crystalline residue
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-fdaa216f322444d4bc902e076e66c78e
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

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