The potent and broad activity of Quinoline has established it as one of the important biologically important scaffold. The present work describes the synthesis of series of quinoline-based heterocyclic schiff bases by the reaction of various substituted 2-chloro-3-formylquinolines with substituted aminopyridines and Isoniazide. The starting compound i.e 2-chloro-3-formylquinolines was synthesized through Vilsmeier-Haack reaction from corresponding acetanilides. All the compounds were characterized by spectroscopic techniques like 1H NMR, IR and mass spectra. The newly synthesized compounds were tested for their antimicrobial and anti-tuberculosis activities. The primarily biological screening results shows that compound 15d showed highest activity against S. auresus and will be emerge as potential anti-microbial agent. The compound 16d displayed the highest anti-tuberculosis activity and presumably will be a potential candidate for further biological studies