Condensation of 4-chlorophenylhydrazine (1) with ethyl  pyruvate led to the formation of ethy1 pyruvate 4- chlorophenyl thydrazone (2) Fischer Indolization of (2) gave ethyl 5-chloro-1H-indole-2-carboxylate (3). Vilsmeier-Hacck formylation of (3) gave ethyl 5-chloro-3-formyl-1H-indole-2-carboxylate (4). The reaction of (4) with substituted anilines led to the formation of ethytl 3-(N-aryliminomethyl)-5-chloro-1H-indole-2-carboxylate (5-10). Structures of the new compounds were confirmed by both analytical and spectral data (IR, NMR and MS). Antimicrobial screening was also performed.