Chloroacetaldehyde → 8-Bromo-6-chloroimidazo(1,2-b)pyridazine

HRID 1024022Notes

Reaction equation

HRID 1024022 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[N:4][C:3]=1[NH2:9].Cl[CH2:11][CH:12]=O>C(O)C>[Br:1][C:2]1[C:3]2[N:4]([CH:11]=[CH:12][N:9]=2)[N:5]=[C:6]([Cl:8])[CH:7]=1

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 220244193-Amino-4-bromo-6-chloropyridazine

Product 1

HCID 468352698-Bromo-6-chloroimidazo(1,2-b)pyridazineYield 107.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-bromo-6-chloropyridazin-3-amine (5.0 g, 24 mmol) and 2-chloroacetaldehyde (12 g, 75 mmol) in ethanol (100 mL) was heated at reflux for 15 h. The reaction mixture was concentrated and washed with acetone (75 mL) to give 104a as a yellow solid (6.0 g, 71%). MS: [M+H]+ 234.

Workup

  1. temperatureat reflux for 15 h
  2. concentrationThe reaction mixture was concentrated
  3. washwashed with acetone (75 mL)

Sources & evidence

ORD record
ord-63b9588283e3404381ff57319d1b4003
Source dataset
uspto-grants-2014_05
Patent number
US08722676B2

Reaction notes

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