3,4-Bis(benzyloxy)-6-[(2-naphthyloxy)methyl]pyridazine → HCID 178516269, compound

HRID 1503217Notes

Reaction equation

HRID 1503217 reaction equation
C([O:8][C:9]1[N:10]=[N:11][C:12]([CH2:23][O:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1>C(O)C.S([O-])([O-])(=O)=O.[Ba+2].[Pd+2].S([O-])([O-])(=O)=O>[OH:8][C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH2:23][O:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=3)[CH:26]=2)[NH:11][N:10]=1

Participants

4

Reactant 1

HCID 1176908243,4-Bis(benzyloxy)-6-[(2-naphthyloxy)methyl]pyridazine

Product 1

HCID 178516269HCID 178516269, compoundYield 41.8%

Reagents, catalysts & solvents 2

HCID 17887766Palladium barium sulphateCatalystHCID 702EthanolSolvent

Procedure

Under a nitrogen atmosphere, 10% palladium-barium sulfate (120 mg) was suspended in ethanol (10 ml), and 3,4-bis(benzyloxy)-6-[(2-naphthyloxy)methyl]pyridazine (120 mg) was added. Under a hydrogen atmosphere, the mixture was stirred at room temperature for 5 hr. The catalyst was filtered off through celite, and the filtrate was concentrated under reduced pressure. The residue was washed with diethyl ether, and the resulting solid was collected by filtration and dried under reduced pressure to give 3-hydroxy-6-[(2-naphthyloxy)methyl]pyridazin-4(1H)-one (30 mg).

Workup

  1. filtrationThe catalyst was filtered off through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. washThe residue was washed with diethyl ether
  4. filtrationthe resulting solid was collected by filtration
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-377b58423aca48b1a84aa97199bf11c3
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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