Methyl iodide → 4-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-one

HRID 572685Notes

Reaction equation

HRID 572685 reaction equation
[Br:1][C:2]1[C:3](=[O:9])[NH:4][N:5]=[C:6]([Cl:8])[CH:7]=1.[C:10](=O)([O-])[O-].[Cs+].[Cs+].IC>CN(C=O)C>[Br:1][C:2]1[C:3](=[O:9])[N:4]([CH3:10])[N:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 115865224-Bromo-6-chloro-2,3-dihydropyridazin-3-one

Product 1

HCID 592164744-Bromo-6-chloro-2-methyl-2,3-dihydropyridazin-3-oneYield 75.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-bromo-6-chloropyridazin-3(2H)-one (10 g, 47.7 mmol, Preparation #27) in DMF (100 mL) was added cesium carbonate (23.34 g, 71.6 mmol, Aldrich) followed by iodomethane (10.17 g, 71.6 mmol) and stirred at RT for about 4 h. The reaction mixture was poured into ice cold water (200 mL) and the product extracted with EtOAc (3×100 mL). The combined organic layers were dried over sodium sulphate and evaporated under reduced pressure to afford 4-bromo-6-chloro-2-methylpyridazin-3(2H)-one 8 g (75%) as brown solid; 1H NMR (400 MHz, CDCl3) δ 7.624 (s, 1H), 3.809 (s, 3H); MS m/z: 222.8 (M+H)+,

Workup

  1. extractionthe product extracted with EtOAc (3×100 mL)
  2. dry with materialThe combined organic layers were dried over sodium sulphate
  3. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-926813fe0747446794a2144d710c0c88
Source dataset
uspto-grants-2015_05
Patent number
US09029409B2

Reaction notes

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