An efficient procedure for the synthesis of chitosan based schiff base and their metal complexes were carried out. Chitosan has both reactive amino and hydroxyl groups. The presence of amino group leads to the synthesis of schiff base (-RC=N) by reaction with aldehydes and ketones. The insertion of functional groups in the chitosan matrix can improve its interaction with metal ions. This work involved the condensation reaction of salicylaldehyde with chitosan and the schiff base formed were complexed with transition metals like Mn, Zn, Ni, and Ag. The synthesized schiff base and their metal complexes were characterized by FTIR and SEM EDX. The metal complexes of chitosan based schiff base were found to act as a heterogeneous catalyst in Knoevenagel reaction. The antibacterial activity of schiff base and its metal complexes against E.coli were compared and the metal complexes were found to have greater antibacterial activity than the schiff base.