2-Ethyl-6,8-dimethyl-3-hydroxymethylimidazo[1,2-b]pyridazine → 2-Ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-carboxaldehyde

HRID 257261Notes

Reaction equation

HRID 257261 reaction equation
[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH2:14][OH:15])[CH3:2].CCOC(C)=O.CCCCCC>C(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH2:1]([C:3]1[N:4]=[C:5]2[C:10]([CH3:11])=[CH:9][C:8]([CH3:12])=[N:7][N:6]2[C:13]=1[CH:14]=[O:15])[CH3:2]

Participants

5

Reactant 2

HCID 197841432-Ethyl-6,8-dimethyl-3-hydroxymethylimidazo[1,2-b]pyridazineHCID 21226206Ethyl acetate hexane

Product 1

HCID 197841562-Ethyl-6,8-dimethylimidazo[1,2-b]pyridazin-3-carboxaldehydeYield 89%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.886 g (4.32 mmol) of the product of Step B dissolved in 15 mL of CH2Cl2 was added 1.772 g of powdered 4A molecular sieves and 4.430 g (51 mmol) of manganese dioxide and the reaction mixture was magnetically stirred at room temperature. After 16 h, TLC analysis (50% EtOAc-hexane) indicated complete reaction and the mixture was filtered. The filtrate was concentrated in vacuo, and the residue was redissolved in 50% EtOAc-hexane and purified by filtration through a short plug of silica gel. Evaporation of the filtrate and drying in vacuo afforded 0.781 g (89%) of the title compound as a tan solid.

Workup

  1. customreaction
  2. filtrationthe mixture was filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionthe residue was redissolved in 50% EtOAc-hexane
  5. filtrationpurified by filtration through a short plug of silica gel
  6. customEvaporation of the filtrate
  7. customdrying in vacuo

Sources & evidence

ORD record
ord-537c5a26403c4a0e899c7072d6eeca0f
Source dataset
uspto-grants-1993_11
Patent number
US05260285

Reaction notes

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