Triphenylphosphine → N-[(4-chlorophenyl)methyl]-1-(3-methylsulfanylpropyl)-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 (396 mg), 3-methylthiolpropanol (0.16 mL) and diethyl azodicarboxylate (0.18 mL). The mixture is stirred at room temperature 48 hours and then concentrated under reduced pressure. The crude product is purified by flash column chromatography eluting with 2% to 6% methanol in dichloromethane and then by recrystallization from toluene-cyclohexane to afford 0.14 gm of the title compound as a white solid.

Provenance & Evidence