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

HRID 456045Notes

Reaction equation

HRID 456045 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 then 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-1efefee5b9164f1ca553432333f181bd
Source dataset
uspto-grants-2013_07
Patent number
US08497368B2

Reaction notes

Loading…