Potassium Iodide → 6-[4-(2-Oxopropoxy)phenyl]-4,5-dihydropyridazin-3(2H)-one

HRID 465446Notes

Reaction equation

HRID 465446 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.Cl[CH2:16][C:17](=[O:19])[CH3:18].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>CC(C)=O>[CH2:16]([O:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1)[C:17]([CH3:18])=[O:19]

Participants

6

Reactant 4

HCID 4875Potassium IodideHCID 6571ChloroacetoneHCID 11430Potassium CarbonateHCID 1358275406-(4-hydroxyphenyl)-4,5-dihydro-3(2H)-pyridazinone

Product 1

HCID 144418546-[4-(2-Oxopropoxy)phenyl]-4,5-dihydropyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4,5-dihydro-6-(p-hydroxyphenyl)-3(2H)pyridazinone (0.55 g), chloroacetone (0.32 g) and potassium carbonate (0.4 g), with a catalytic amount of potassium iodide, was stirred and heated under reflux in acetone (60 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 a gum which was purified by chromatography on Silica gel. Elution with methanol-chloroform (4:96) gave 4,5-dihydro-6-(4-acetonyloxyphenyl)-3(2H)-pyridazinone as a pale yellow 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 to a gum which
  6. customwas purified by chromatography on Silica gel
  7. washElution with methanol-chloroform (4:96)

Sources & evidence

ORD record
ord-443f291e23b44c30b58574d54517d109
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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