Methanol → HCID 178518824, compound

HRID 1503216Notes

Reaction equation

HRID 1503216 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][C:28]([Cl:31])=[CH:27][CH:26]=2)=[CH:13][C:14]=1[O:15]CC1C=CC=CC=1)C1C=CC=CC=1.B(Br)(Br)Br.CO>ClCCl>[Cl:31][C:28]1[CH:29]=[CH:30][C:25](/[CH:24]=[CH:23]/[C:12]2[CH:13]=[C:14]([OH:15])[C:9](=[O:8])[NH:10][N:11]=2)=[CH:26][CH:27]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 25134Boron tribromideHCID 71655737HCID 71655737, compound

Product 1

HCID 178518824HCID 178518824, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution (5 mL) of 3,4-bis(benzyloxy)-6-[(E)-2-(4-chlorophenyl)vinyl]pyridazine (150 mg) in dichloromethane was added a solution (770 μL) of 1M boron tribromide in dichloromethane at −78° C. and the mixture was stirred at 0° C. for 3 hr. Methanol was added to terminate the reaction, and the solvent was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform-methanol) and the obtained solid was washed with ethanol-water, collected by filtration and dried under reduced pressure to give 6-[(E)-2-(4-chlorophenyl)vinyl]-4-hydroxypyridazin-3(2H)-one (58 mg).

Workup

  1. customto terminate
  2. customthe reaction
  3. concentrationthe solvent was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (chloroform-methanol)
  5. washthe obtained solid was washed with ethanol-water
  6. filtrationcollected by filtration
  7. customdried under reduced pressure

Sources & evidence

ORD record
ord-82db5c03900745dfac2fc64f3fc50142
Source dataset
uspto-grants-2015_12
Patent number
US09212147B2

Reaction notes

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