Methyl iodide → 5-Chloro-2-methylpyridazin-3(2H)-one

HRID 57850

Reaction equation

HRID 57850 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][NH:5][C:6](=[O:8])[CH:7]=1.IC.[C:11](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[N:4][N:5]([CH3:11])[C:6](=[O:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 199057185-Chloropyridazin-3(2H)-one

Product 1

HCID 129101445-Chloro-2-methylpyridazin-3(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-chloro-1H-pyridazin-6-one (6.000 mmol; 783.2 mg), Iodomethane (7.200 mmol; 1032 mg; 0.453 mL), and potassium carbonate (9.000 mmol; 1256 mg) in DMF (12 mL) was stirred at room temperature overnight. The mixture was filtered. The filtrate was partitioned between EtOAc and water. The organic layer was concentrated. The residue was purified on silica eluted with 0 to 40% EtOAc in DCM to afford 5-chloro-2-methyl-pyridazin-3-one as an off-white solid (514.7, 59%).

Workup

  1. filtrationThe mixture was filtered
  2. customThe filtrate was partitioned between EtOAc and water
  3. concentrationThe organic layer was concentrated
  4. customThe residue was purified on silica
  5. washeluted with 0 to 40% EtOAc in DCM

Sources & evidence

ORD record
ord-629f6a2a648d414ab2141a7d9626c816
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Linked notes

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