P. O’Neill, R. Storr, B. Park
Apr 30, 1998
Citations
0
Influential Citations
25
Citations
Journal
Tetrahedron
Abstract
Several approaches to the synthesis of 5-fluoro-6-methoxy-8-nitroquinoline 5, the key intermediate required for the synthesis of 5-fluoroprimaquine, were investigated. In one approach, 5-chloro-6-methoxy-8-nitroquinoline was synthesised and treated with a variety of nucleophilic sources of fluoride. In another approach, electrophilic substitution of 6-methoxy-8-nitroquinoline with (N-fluorosulfonimide, NFSI) was investigated. The final approach to 5 involved a modified Skraup reaction of 5-fluoro-4-methoxy-2-nitroaniline which gave the required intermediate in 30% yield.