Diethylene Glycol → N-[(4-chlorophenyl)methyl]-1-[2-(2-hydroxyethoxy)ethyl]-6-(morpholinomethyl)-4-oxo-quinoline-3-carboxamide

Participants

Reaction Steps

A dry flask containing N-(4-chlorobenzyl)-4-hydroxy-6-(4-morpholinylmethyl)-3-quinolinecarboxamide (0.20 gm) from Preparation No. 40 in dry THF (5 mL) under an argon atmosphere is added triphenylphosphine (165 mg), diethyleneglycol (0.20 mL) and diethyl azodicarboxylate (0.10 mL). The mixture is stirred at room temperature for 2 hrs. The reaction mixture is concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 10% to 40% methanol in ethyl acetate and then by recrystallization from ethyl acetate to afford 68 mg of the title compound as a white solid.

Provenance & Evidence