4,5-dihydro-6-[4-(2-hydroxypropyl)-phenyl]-3(2H)-pyridazinone → 4,5-dihydro-6-[(4-acetonyl)phenyl]-3(2H)-pyridazinone

HRID 465449Notes

Reaction equation

HRID 465449 reaction equation
[OH:1][CH:2]([CH3:17])[CH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH2:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:6][CH:5]=1.[Cr](Cl)([O-])(=O)=O.[NH+]1C=CC=CC=1>ClCCl>[CH2:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:11][CH2:12][C:13](=[O:16])[NH:14][N:15]=2)=[CH:8][CH:9]=1)[C:2]([CH3:17])=[O:1]

Participants

4

Reactant 2

HCID 198745634,5-dihydro-6-[4-(2-hydroxypropyl)-phenyl]-3(2H)-pyridazinoneHCID 178418287HCID 178418287, compound

Product 1

HCID 542657524,5-dihydro-6-[(4-acetonyl)phenyl]-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4,5-dihydro-6-[4-(2-hydroxypropyl)-phenyl]-3(2H)-pyridazinone (0.23 g) and pyridiniumchlorochromate (0.21 g) in dichloromethane (20 ml) was stirred at ambient tempeature for 18 hr., filtered and evaporated to a gum which was chromatographed on slice gel. Elution with 4% MeOH in CHCl3 gave 4,5-dihydro-6-[(4-acetonyl)phenyl]-3(2H)-pyridazinone as a crystalline solid.

Workup

  1. filtration, filtered
  2. customevaporated to a gum which
  3. customwas chromatographed on slice gel
  4. washElution with 4% MeOH in CHCl3

Sources & evidence

ORD record
ord-eb0fa30c90cd472cbeebb36ff1f22630
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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