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

HRID 465451Notes

Reaction equation

HRID 465451 reaction equation
C([O:4][CH:5]([CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:14][CH2:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1)(=O)C.Cl>[OH-].[Na+]>[OH:4][CH:5]([CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH2:14][CH2:15][C:16](=[O:19])[NH:17][N:18]=2)=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 198745154,5-dihydro-6-[4-(2-acetoxypropyl)phenyl]-3(2H)-pyridazinone

Product 1

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

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

4,5-Dihydro-6-[4-(2-acetoxypropyl)phenyl]-3(2H)pyridazinone (0.73 g) was heated under reflux in 2N sodium hydroxide solution for 2 hr, cooled, neutralised with 2N hydrochloric acid, and extracted into ethyl acetate. The organic extract was dried (MgSO4) and evaporated to an oil which was chromatographed on silica gel. Elution with methanol-chloroform (4:96) gave 4,5-dihydro-6-[4-(2-hydroxypropyl)phenyl]-3(2H)pyridazinone as a white solid.

Workup

  1. temperaturecooled
  2. extractionextracted into ethyl acetate
  3. extractionThe organic extract
  4. dry with materialwas dried (MgSO4)
  5. customevaporated to an oil which
  6. customwas chromatographed on silica gel
  7. washElution with methanol-chloroform (4:96)

Sources & evidence

ORD record
ord-eb1a9297951e478e946dd34458e1685b
Source dataset
uspto-grants-1992_10
Patent number
US05153210

Reaction notes

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