Methyl iodide → 6-Chloro-2-methyl-2,3-dihydropyridazin-3-one
Reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][N:7]=1.[C:9]([O-])([O-])=O.[Cs+].[Cs+].CI>CC#N>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH3:9])[N:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
To a solution of 6-chloropyridazin-3(2H)-one (780 mg, 6 mmol) in CH3CN (40 mL) was added Cs2CO3 (3.9 g, 12 mmol) and CH3I (1 mL, 12 mmol) and the reaction mixture was stirred at 70° C. overnight. Solid was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (hexane/EA=3/1) to afford the title compound as orange oil (6.5 g, 75%). [LCMS: Rt=1.43 min, m/z 145.1 (M+H)+].
Workup
- customSolid was removed by filtration
- concentrationthe filtrate was concentrated under reduced pressure
- customThe residue was purified by silica gel chromatography (hexane/EA=3/1)
Sources & evidence
- ORD record
- ord-7997c72e78a14be2a72752afc37afc7e
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09273026B2
Reaction notes
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