Hydrochloric Acid → 5-(benzyloxy)pyridazin-3(2H)-one

HRID 564046Notes

Reaction equation

HRID 564046 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[N:13][N:12](C2CCCCO2)[C:11](=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>CO>[CH2:1]([O:8][C:9]1[CH:14]=[N:13][NH:12][C:11](=[O:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 670073955-(Benzyloxy)-2-(2-tetrahydropyranyl)pyridazin-3(2H)-one

Product 1

HCID 598221075-(benzyloxy)pyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 500 mg (1.75 mmol) 5-benzyloxy-2-(tetrahydro-pyran-2-yl)-2H-pyridazin-3-one (preparation 5b) in 10 mL MeOH is added 8.73 mL (8.73 mmol) 1M aqueous HCl solution and the reaction mixture is stirred overnight at RT and 10 h at reflux. MeOH is evaporated, to the residual aqueous phase is added saturated aqueous NaHCO3-solution until the solution is basic. The aqueous phase is extracted with EtOAc, the combined organic phase is washed with water, dried over MgSO4, filtered and evaporated to afford the product.

Workup

  1. temperatureat reflux
  2. customMeOH is evaporated, to the residual aqueous phase
  3. additionis added saturated aqueous NaHCO3-solution until the solution
  4. extractionThe aqueous phase is extracted with EtOAc
  5. washthe combined organic phase is washed with water
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. customevaporated
  9. customto afford the product

Sources & evidence

ORD record
ord-e5c071b8dd32482c853b15b258d4059d
Source dataset
uspto-grants-2011_11
Patent number
US08067590B2

Reaction notes

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