Methyl iodide → 6-Chloro-2-methyl-2,3-dihydropyridazin-3-one

HRID 919293Notes

Reaction equation

HRID 919293 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.[K+].[K+].CI>C(#N)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5](=[O:8])[N:6]([CH3:9])[N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2528286-Chloropyridazin-3-ol

Product 1

HCID 27836076-Chloro-2-methyl-2,3-dihydropyridazin-3-one

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution 6-chloropyridazin-3(2H)-one (130 mg, 1.0 mmol) in acetonitrile (3.0 mL) was added K2CO3 (437 mg, 3.16 mmol), CH3I (299 mg, 2.11 mmol), the reaction mixture was stirred at reflux for 2 h. The mixture was cooled to ambient temperature, diluted with EtOAc (20 mL), washed with sodium bicarbonate (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was purified with silica gel column (Petroleum ether:ethyl acetate=4:1) to obtained product: LC/MS m/z=145 (M+H)+.

Workup

  1. temperatureat reflux for 2 h
  2. washwashed with sodium bicarbonate (10 mL) and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column (Petroleum ether:ethyl acetate=4:1)
  7. customto obtained product

Sources & evidence

ORD record
ord-8a9f4b1f7eea4bc698fd87d0c961aa8d
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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