1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-ol → 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-one

HRID 2426522Notes

Reaction equation

HRID 2426522 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]([CH:10]([OH:13])[CH2:11][CH3:12])[CH:3]=1>O1CCCC1.[O-2].[O-2].[Mn+4]>[Cl:1][C:2]1[N:7]=[N:6][C:5]([O:8][CH3:9])=[C:4]([C:10](=[O:13])[CH2:11][CH3:12])[CH:3]=1

Participants

4

Reactant 1

HCID 102622801-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-ol

Product 1

HCID 230924891-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

12.25 g 1-(6-Chloro-3-methoxy-pyridazin-4-yl)-propan-1-ol is dissolved in 410 ml tetrahydrofuran and 105 g of manganese dioxide is added. The reaction is stirred for 24 h at RT. Solids are removed by filtration, and the solution is treated with a further 105 g of manganese dioxide for 16 h at RT. Solids are removed by filtration, and the solvent is removed under reduced pressure. The product is purified by silica gel chromatography, eluting with a gradient of ethyl acetate in heptane. Yield 3.25 g. LC-MS (ES+) 201 (M+H)+.

Workup

  1. customSolids are removed by filtration
  2. additionthe solution is treated with a further 105 g of manganese dioxide for 16 h at RT
  3. customSolids are removed by filtration
  4. customthe solvent is removed under reduced pressure
  5. customThe product is purified by silica gel chromatography
  6. washeluting with a gradient of ethyl acetate in heptane

Sources & evidence

ORD record
ord-b36dea8a7d294bddb4851fbe5a832518
Source dataset
uspto-grants-2011_06
Patent number
US07968546B2

Reaction notes

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