2-t-butyl-4-chloro-5-dimethylamino-3(2H)-pyridazinone → 2-t-butyl-5-dimethylamino-3(2H)-pyridazinone

HRID 1291220Notes

Reaction equation

HRID 1291220 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9](Cl)=[C:8]([N:13]([CH3:15])[CH3:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([N:5]1[C:10](=[O:11])[CH:9]=[C:8]([N:13]([CH3:15])[CH3:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 189188582-t-butyl-4-chloro-5-dimethylamino-3(2H)-pyridazinone

Product 1

HCID 189189072-t-butyl-5-dimethylamino-3(2H)-pyridazinone

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In methanol (40 ml) was dissolved 2-t-butyl-4-chloro-5-dimethylamino-3(2H)-pyridazinone (4.3 g) followed by addition of 10% palladium-on-carbon (water content 50%) (430 mg), and the mixture was stirred under hydrogen at room temperature for 48 hours. The catalyst was then filtered off and the filtrate was concentrated. To the residue was added saturated aqueous NaHCO3 solution and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, and concentrated to dryness. The residue was washed with n-hexane and dried. White powder, 3.4 g. 1H-NMR (CDC13) 6: 1.63(9H,s), 2.98(6H,s), 5.65(1H,d,J=3.OHz), 7.55(1H,d,J=3.0Hz).

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated
  3. additionTo the residue was added saturated aqueous NaHCO3 solution
  4. extractionthe mixture was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated to dryness
  8. washThe residue was washed with n-hexane
  9. customdried

Sources & evidence

ORD record
ord-0bcd0aa615b94f0a8b2260f2032910dc
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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