Grinding technique as a method employing green chemistry was selected for the synthesis of Schiff bases from 5-aminosalicylic acid and substituted benzaldehydes. Two known and eight novel 5-aminosalicylic acid Schiff bases were synthesized and recrystallized using methanol. All the compounds were characterized by their physical data and spectral studies such as IR, 1 H NMR, 13 C NMR and Mass. The synthesized compounds were evaluated for in vitro antioxidant activity by scavenging 1,1-diphenyl-2picrylhydrazyl (DPPH) and nitric oxide free radicals at 100μM concentration. The activity data revealed that the compounds with 4-hydroxy-3,5-dimethoxy substitution and 3,4-methylenedioxy substitution on N-benzylidene ring showed highest antioxidant activity in DPPH and nitric oxide scavenging models respectively. The activity of these compounds was found to be greater than 5-aminosalicylic acid and the standards employed. All the compounds were evaluated for antibacterial activity by agar well diffusion method using gram negative and gram positive bacteria such as E. coli, P. aeruginosa, S. aureus and B. subtilis. The results indicate that the evaluated compounds showed good to moderate antibacterial activity.