Ll. Lai et al., SUBSTITUENT EFFECT ON THE CHLORINATION OF 2-ALKOXYPYRIDINES TO GIVE 2-CHLOROPYRIDINES UNDER VILSMEIER-HAACK CONDITIONS, Journal of chemical research. Synopses, (4), 1996, pp. 194-195
Various substituted 2-alkoxypyridines were converted into the correspo
nding 2-chloropyridines in 28-91% yields by use of POCl3 and DMF, in w
hich the methyl, halogen, ester and nitro groups displayed an activati
ng effect; in contrast, an amino group exhibited a deactivating effect
.