3,4-bis(benzyloxy)-6-[(E)-2-phenylvinyl]pyridazine → HCID 178515965, compound

HRID 1503215Notes

Reaction equation

HRID 1503215 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12](/[CH:23]=[CH:24]/[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>C(O)C.[C].[Pd]>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[NH:11][N:10]=1

Participants

4

Reactant 1

HCID 1176911273,4-bis(benzyloxy)-6-[(E)-2-phenylvinyl]pyridazine

Product 1

HCID 178515965HCID 178515965, compoundYield 40.2%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolvent

Procedure

To a solution (8 mL) of 3,4-bis(benzyloxy)-6-[(E)-2-phenylvinyl]pyridazine (272 mg) in ethanol was added 10% palladium-carbon (90 mg), and the mixture was stirred under a hydrogen atmosphere at room temperature for 4 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure. To the residue was added ethyl acetate-chloroform, and the resulting solid was collected by filtration and dried under reduced pressure to give 3-hydroxy-6-(2-phenylethyl)pyridazin-4(1H)-one (60 mg).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. additionTo the residue was added ethyl acetate-chloroform
  4. filtrationthe resulting solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-2fb10f5d39a34dfe9109ef2017eb1a83
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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