M. Reuman et al., CYANIDE MEDIATED DECARBOXYLATION OF 1-SUBSTITUTED-4-OXOQUINOLINE AND 4-ORO-1,8-NAPHTHYRIDINE-3-CARBOXYLIC ACIDS, Tetrahedron letters, 35(45), 1994, pp. 8303-8306
Electron deficient 3-quinolinecarboxylic acids undergo ready decarboxy
lation in the presence of cyanide ion. This reaction most likely requi
res the addition of CN- to the 2-position of the quinoline (or naphthy
ridine) nucleus to provide a beta-keto acid intermediate that rapidly
decarboxylates to give the 3-H substituted product.