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

HRID 1747799Notes

Reaction equation

HRID 1747799 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

Procedure

3-Chloro-5-methoxypyridazin-4-ol (10.0 g) was dissolved in DMF (300 mL), NaH (3.26 g, 55 wt %) and tetrabutylammoniumiodide (4.60 g) were added at 0° C., and the mixture was stirred at the same temperature for 10 min. To the reaction mixture was added benzylbromide (12.3 g) at 0° C., and the mixture was stirred at room temperature for 20 hr. The reaction mixture was diluted with water, extracted with dichloromethane, washed with water and saturated brine, dried over anhydrous sodium sulfate, filtered, concentrated, and 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. extractionextracted with dichloromethane
  3. washwashed with water and saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customrecrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-24469635a0c54183a29e172b71aa934f
Source dataset
uspto-grants-2015_10
Patent number
US09150588B2

Reaction notes

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