Chloroacetaldehyde → 6,8-Dichloroimidazo[1,2-b]pyridazine
Reaction equation
[NH2:1][C:2]1[N:3]=[N:4][C:5]([Cl:9])=[CH:6][C:7]=1[Cl:8].[CH:10](O)(C)[CH3:11].ClCC=O>O>[Cl:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]2[N:3]([CH:10]=[CH:11][N:1]=2)[N:4]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A mixture of 3-amino-4,6-dichloropyridazine (0.315 g, 1.92 mmol), 3 mL of isopropanol and 0.5 mL of a 50% chloroacetaldehyde in water solution was stirred at 80° C. for 20 h, then concentrated to remove isopropanol. The resulting yellow mixture was treated with 10 mL of a saturated aq. NaHCO3 solution and extracted with two 10 mL portions of dichloromethane. The combined organic layers were dried over MgSO4, filtered and concentrated to a yellow oil. Column chromatography (0->33% EtOAc/hexanes) afforded 0.313 g (87%) of 6,8-dichloro-imidazo[1,2-b]pyridazine as a light yellow solid.
Workup
- concentrationconcentrated
- customto remove isopropanol
- additionThe resulting yellow mixture was treated with 10 mL of a saturated aq. NaHCO3 solution
- extractionextracted with two 10 mL portions of dichloromethane
- dry with materialThe combined organic layers were dried over MgSO4
- filtrationfiltered
- concentrationconcentrated to a yellow oil
Sources & evidence
- ORD record
- ord-9c9a4425adae4a9d8f4cc359974e11ad
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08426441B2
Reaction notes
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