Formaldehyde → (6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanol

HRID 1959636Notes

Reaction equation

HRID 1959636 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:8]=[CH:9][N:10]=2)[N:7]=1.C[C:12]([O-])=[O:13].[Na+].C=O>CC(O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8]([CH2:12][OH:13])=[CH:9][N:10]=2)[N:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-HCID 517045Sodium Acetate

Product 1

HCID 57352521(6-Chloroimidazo(1,2-b)pyridazin-3-yl)methanolYield 72.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 6-chloroimidazo[1,2-b]pyridazine (1.5 g, 9.8 mmol) in AcOH (50 mL) was added NaOAc (1.4 g, 17.1 mmol) and paraformaldehyde (1.5 g). The mixture was heated at reflux overnight and concentrated under reduced pressure. The residue was basified to pH 12. Then the mixture was filtered and the solid was washed with EtOH to afford (6-chloro-imidazo[1,2-b]pyridazin-3-yl)-methanol (1.3 g) in 72% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationconcentrated under reduced pressure
  4. filtrationThen the mixture was filtered
  5. washthe solid was washed with EtOH

Sources & evidence

ORD record
ord-0c7257dbf4e144f0ac646a4cd835a48c
Source dataset
uspto-grants-2013_04
Patent number
US08410264B2

Reaction notes

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