Potassium Hydroxide → 1-(4-Amino-2,6-dimethoxyphenyl)ethan-1-one

HRID 326308Notes

Reaction equation

HRID 326308 reaction equation
C([NH:4][C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([C:13](=[O:15])[CH3:14])=[C:7]([O:16][CH3:17])[CH:6]=1)(=O)C.[OH-].[K+]>C(O)C>[NH2:4][C:5]1[CH:6]=[C:7]([O:16][CH3:17])[C:8]([C:13](=[O:15])[CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 69353411HCID 69353411, compound2×

Product 1

HCID 576784271-(4-Amino-2,6-dimethoxyphenyl)ethan-1-oneYield 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of (4'-acetylamino-2',6'-dimethoxyphenyl)ethanone (compound 75-1) (7.11 g, 0.03 mol) and 10% potassium hydroxide solution in ethanol is heated to reflux for 3 hours. The solvent is distilled from the reaction mixture under reduced pressure. The residue is dissolved in dichloromethane, and the solution is washed with water, dried, and concentrated. The residue is placed on a silica gel column and eluted with a mixture of ethylacetate and dichloromethane (1:1) to yield the title compound as a crystalline solid (5.54 g, 95%, m.p.=154°-155° C.).

Workup

  1. temperatureis heated
  2. temperatureto reflux for 3 hours
  3. distillationThe solvent is distilled from the reaction mixture under reduced pressure
  4. dissolutionThe residue is dissolved in dichloromethane
  5. washthe solution is washed with water
  6. customdried
  7. concentrationconcentrated
  8. washeluted with a mixture of ethylacetate and dichloromethane (1:1)

Sources & evidence

ORD record
ord-09c79e59187344329a0921d08eee5162
Source dataset
uspto-grants-1993_12
Patent number
US05268386

Reaction notes

Loading…