Benzyl Bromide → 1-benzyl-3-chloro-5-methoxypyridazin-4(1H)-one

HRID 1528076Notes

Reaction equation

HRID 1528076 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([O:9][CH3:10])[C:7]=1[OH:8].[H-].[Na+].[CH2:13](Br)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:13]([N:4]1[CH:5]=[C:6]([O:9][CH3:10])[C:7](=[O:8])[C:2]([Cl:1])=[N:3]1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 178493809HCID 178493809, compound

Product 1

HCID 866865601-benzyl-3-chloro-5-methoxypyridazin-4(1H)-oneYield 126.8%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

3-Chloro-5-methoxypyridazin-4-ol (10.0 g) was dissolved in DMF (300 mL), sodium hydride (3.26 g, 55 wt %) and tetrabutylammonium iodide (4.60 g) were added thereto at 0° C., and the mixture was stirred at the same temperature for 10 min. To the reaction mixture was added benzyl bromide (12.3 g) at 0° C., and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with water, and the mixture was extracted with dichloromethane. The extract was washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, and concentrated. The residue was recrystallized from ethyl acetate/hexane to give the title compound (19.8 g).

Workup

  1. stirringthe mixture was stirred at room temperature for 20 hr
  2. extractionthe mixture was extracted with dichloromethane
  3. washThe extract was washed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-95080da3061d4b09a4330cdf51926902
Source dataset
uspto-grants-2015_07
Patent number
US09090586B2

Reaction notes

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