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

HRID 1162148Notes

Reaction equation

HRID 1162148 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH2:8])=[CH:4][CH:3]=1.Cl[CH2:10][CH:11]=O>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH:10]=[CH:11][N:8]=2)[N:7]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 216436-Amino-3-chloropyridazine

Product 1

HCID 138828Imidazo(1,2-b)pyridazine, 6-chloro-Yield 52.1%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 6-chloro-pyridazinamine (5.00 g, 38 mmol) in 1-butanol (5 mL) was treated with chloroacetaldehyde (50% in water, 5.0 mL, 38 mmol) and the tan suspension was refluxed two hours and to give a dark solution. The reaction mixture was cooled to room temperature and the solid was collected by filtration and washed with methanol to afford a brown solid (3.04 g); evaporation of the filtrate gave additional product (4.60 g). The solids were combined (7.64 g) and used in the next reaction without further purification: MS [M+H]+ 154.

Workup

  1. temperaturethe tan suspension was refluxed two hours
  2. customto give a dark solution
  3. filtrationthe solid was collected by filtration
  4. washwashed with methanol

Sources & evidence

ORD record
ord-86bcdbe5ce7d4562956582d2b7f184e0
Source dataset
uspto-grants-2010_10
Patent number
US07820670B2

Reaction notes

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