Eleven enamides were prepared by adopting different procedures. The various enamides prepared were subjected to Vilsmeier reaction using (i) POCl3/DMF;(ii) diphosgene/DMF;(iii) triphosgene/DMF leading to the formation of various multisubstituted chloronicotinaldehydes . Studies carried out indicate that Vilsmeier reagent concentration and the replacement of POCl3 by diphosgene or triphosgene, provides excellent selectivity and higher yields. ...