Phthalimide → 6-[4-(3-aminopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)-pyridazinone

Participants

Reaction Steps

A mixture of 0.997 g (2.55 mmol) of the phthalimide prepared above, 124 microliters (2.55 mmol) of 98% hydrazine monohydrate, and 25 ml of ethanol is heated at reflux under N2 overnight. TLC (90:10 CHCl3 :CH3OH) of the reaction mixture showed some phthalimide still present. An additional 25 ml of hydrazine was added, and the mixture heated at reflux for 3 hrs. The solvent is removed under vacuum, the residue taken up in about 10 ml of CH3OH and flash chromatographed on silica gel (90:10:2 CHCl3 :CH3OH:NH4OH) to give 531 mg of 6-[4-(3-aminopropyloxy)phenyl]-5-methyl-4,5-dihydro-3(2H)pyridazinone as a white solid. Yield 80%.

Provenance & Evidence