Potassium Iodide → 3,4-dihydro-5-(4-acetonyloxyphenyl) 6-methyl-2(1H)-pyridinone

HRID 465448Notes

Reaction equation

HRID 465448 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:15])[NH:12][C:13]=2[CH3:14])=[CH:4][CH:3]=1.Cl[CH2:17][C:18](=[O:20])[CH3:19].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:17]([O:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:15])[NH:12][C:13]=2[CH3:14])=[CH:6][CH:7]=1)[C:18]([CH3:19])=[O:20]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 132689765-(4-Hydroxyphenyl)-6-methyl-3,4-dihydropyridin-2(1H)-one

Product 1

HCID 198745663,4-dihydro-5-(4-acetonyloxyphenyl) 6-methyl-2(1H)-pyridinone

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 3,4-dihydro-5-(4-hydroxyphenyl)-6-methyl-2(1H)-pyridinone (0.94 g), chloroacetone (0.43 g) and potassium carbonate (0.64 g), with a catalytic amount of potassium iodide, was stirred and heated under reflux in acetone (80 ml) for 16 hr. The solvent was evaporated and the residue partitioned between water and ethyl acetate. The organic layer was dried (MgSO4) and evaporated to give 3,4-dihydro-5-(4-acetonyloxyphenyl)-6-methyl-2(1H)-pyridinone as a solid.

Workup

  1. temperatureheated
  2. customThe solvent was evaporated
  3. customthe residue partitioned between water and ethyl acetate
  4. dry with materialThe organic layer was dried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-8e9de204cc9f4536ae735588dc99832d
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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