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

HRID 1479938Notes

Reaction equation

HRID 1479938 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 chloroacetaldehyde (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 brine 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 brine
  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-6f1c10914c7e4d20af5db61142bd97e3
Source dataset
uspto-grants-2016_08
Patent number
US09409889B2

Reaction notes

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