Bromoacetone → 6-Chloro-2-methylimidazo(1,2-b)pyridazine

HRID 2051109Notes

Reaction equation

HRID 2051109 reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:8])=[CH:6][CH:7]=1.Br[CH2:10][C:11](=O)[CH3:12]>C(O)CC>[Cl:8][C:5]1[CH:6]=[CH:7][C:2]2[N:3]([CH:10]=[C:11]([CH3:12])[N:1]=2)[N:4]=1

Participants

4

Reactant 2

HCID 11715BromoacetoneHCID 216436-Amino-3-chloropyridazine

Product 1

HCID 104420726-Chloro-2-methylimidazo(1,2-b)pyridazineYield 48.8%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

A solution of 13.0 g of 3-amino-6-chloropyridazine, 15.2 g of bromoacetone in 200 ml of propanol is heated under reflux for 3 hours. After cooling, the precipitated crystals are collected by filtration and dissolved in 100 ml of water. The solution is neutralized with potassium carbonate and the precipitated crystals are collected by filtration. Upon recrystallization from ethanol, it affords 8.2 g of the title compound having mp. 131° C.

Workup

  1. temperatureunder reflux for 3 hours
  2. temperatureAfter cooling
  3. filtrationthe precipitated crystals are collected by filtration
  4. dissolutiondissolved in 100 ml of water
  5. filtrationthe precipitated crystals are collected by filtration
  6. customUpon recrystallization from ethanol, it

Sources & evidence

ORD record
ord-1333ee224cd349c09da9e02cccffd99c
Source dataset
uspto-grants-1991_05
Patent number
US05017212

Reaction notes

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