Triphenylphosphine → N-[(4-chlorophenyl)methyl]-1-[2-(2-ethoxyethoxy)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 (164 mg), 2-ethoxy-(2-ethoxy)ethanol (0.09 mL) and diethyl azodicarboxylate (0.10 mL). The mixture is stirred at room temperature overnight. The reaction mixture is again treated with triphenylphosphine (164 mg), 2-ethoxy-(2-ethoxy)ethanol (0.09 mL) and diethyl azodicarboxylate (0.10 mL). After 4 hours, the reaction mixture is concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with acetone and then by recrystallization from ethyl acetate-heptane to afford 0.18 gm of the title compound as a white solid.

Provenance & Evidence