Chloroacetaldehyde → Imidazo(1,2-b)pyridazine, 6-chloro-

HRID 2353048Notes

Reaction equation

HRID 2353048 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Cl[CH2:10][CH:11]=O.C(=O)(O)[O-].[Na+]>C(O)CCC>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[N:4]=1

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 216436-Amino-3-chloropyridazineHCID 516892Sodium Bicarbonate

Product 1

HCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-Yield 70.3%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5.0 g (38.6 mmol) of 3-amino-6-chloropyridazine were heated together with 4.7 ml (40 mmol) of chloracetaldehyde (55% strength in water) in 15 ml of n-butanol at 120° C. for a period of 5 days. After the reaction was complete, the reaction mixture was added to saturated sodium bicarbonate solution and extracted three times with ethyl acetate. The combined organic phases were then washed with sat. sodium chloride solution and dried over sodium sulfate, and the solvent was removed in vacuo. In the final purification by chromatography on silica gel, 4.17 g (70%) of the desired product were isolated in the form of an amorphous white solid.

Workup

  1. extractionextracted three times with ethyl acetate
  2. washThe combined organic phases were then washed with sat. sodium chloride solution
  3. dry with materialdried over sodium sulfate
  4. customthe solvent was removed in vacuo
  5. customIn the final purification by chromatography on silica gel

Sources & evidence

ORD record
ord-bdc0c428a8b04519882dc980b2822f25
Source dataset
uspto-grants-2010_07
Patent number
US07750000B2

Reaction notes

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