Chloroacetaldehyde → 6-Chloro-7-methylimidazo[1,2-b]pyridazine

HRID 2370044Notes

Reaction equation

HRID 2370044 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][C:3]=1[CH3:9].Cl[CH2:11][CH:12]=O>C(O)CCC>[Cl:1][C:2]1[C:3]([CH3:9])=[CH:4][C:5]2[N:6]([CH:11]=[CH:12][N:8]=2)[N:7]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 123536636-Chloro-5-methylpyridazin-3-amine

Product 1

HCID 122483366-Chloro-7-methylimidazo[1,2-b]pyridazineYield 33.4%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

6-chloro-5-methylpyridazin-3-amine 7 (0.6 g, 4.18 mmol) was dissolved in n-butanol (10 ml) and chloroacetaldehyde (0.328 g, 4.18 mmol) was added. The reaction was refluxed for 6 hrs and n-butanol was removed under reduced pressure. The crude product was purified by column chromatography (DCM/hexane, 70:30) to afford compound 8 (0.234 g, yield=33.4%).

Workup

  1. temperatureThe reaction was refluxed for 6 hrs
  2. customn-butanol was removed under reduced pressure
  3. customThe crude product was purified by column chromatography (DCM/hexane, 70:30)

Sources & evidence

ORD record
ord-628d679f24a04e08b2af763659ac6b14
Source dataset
uspto-grants-2014_04
Patent number
US08710057B2

Reaction notes

Loading…