One-pot synthesis of N-benzyl-2-aminobenzoic acid, via ring opening of isatoic anhydride derivative, and its antibacterial screening

Abstract

2-(N-Benzyl) amino benzoic acid is a bifunctional molecule that could be produced from the reaction between isatoic anhydride and aryl halide. Analogues and derivatives of isatoic anhydride have wide application in pharmaceuticalsincluding antibacterial activity. The aim of this study is to synthesize, characterize and screen N-benzyl isatoic anhydride and 2-(N-benzyl) amino benzoic acid for antibacterial activity. The reaction of isatoic anhydride and benzyl bromide in the presence of potassium carbonate in DMSO at room temperature yielded N-benzyl isatoic anhydride, which under hydrolysis yielded 2-(N-benzyl) amino benzoic acid in which the anhydride ring is opened up. This compound was screened against Gram positive and negative bacteria. Moderate yield of 2-(N-benzyl) amino benzoic acid, a yellow crystal (melting point of 160-162oC, percentage yield 65 %, Rf 0.19) formed by ring opening of N-benzyl isatoic anhydride. The compound showed no antibacterial activity against Escherichia coli, Staphylococcus aureus, Pseudomonas pyocyanea, Salmonella typhimurium, Klebsiella aeruginosa and Bacillus subtilis. 2-(N-benzyl)amino benzoic was synthesized, characterized and showed no activity against bacteria.