Water → HCID 19436784, compound

Participants

Reaction Steps

3-[[3-(Difluoromethyl)-1-methyl-1H-pyrazol-5-yl]oxy]-5-methoxypyridazine (Compound No. 45, 4.5 g, 0.017 mole) and dichloromethane (80 mL) were stirred and cooled with a water bath while aluminum chloride (4.3 g, 0.031 mole, (note: this aluminum chloride was old and wet) was added and the mixture was then stirred at room temperature for 5 hours. The mixture was poured into cold water and the aqueous phase washed three times with dichloromethane. The pH of the aqueous phase was adjusted to 4, using 10% sodium hydroxide; and the product was extracted with ethyl acetate. The extracts were dried with magnesium sulfate, filtered and concentrated in vacuo. The residue was purified by chromatography on silica gel to give 5-[(5-methoxy-3-pyridazinyl)oxy]-1-methyl-1H-pyrazole-3-carboxaldehyde (0.50 g, 12% yield) as white solid.

Provenance & Evidence