Abstract
3-Fluoroquinoline 1-oxide, which was prepared through the Schiemann reaction of 3-aminoquinoline, followed by N-oxygenation, was nitrated to 3-fluoro-4-nitroquinoline 1-oxide. The fluorine atom of this compound was replaced with nucleophiles such as OR- or NR2-containing compounds in neutral or alkaline media to afford 3-substituted 4-nitroquinoline 1-oxide derivatives. The reaction with aqueous hydrogen chloride brought about the replacement of the nitro group to give 3-fluoro-4-chloroquinoline 1-xoide.
