Vaniline [1] is nitrated by using known literature method to 4-hydroxy-3-methoxy-5-nitrobenzaldehyde [2]. The haloanilines [3a-g] used for the synthesis of Schiff bases was synthesized by known literature methods and by referring Vogel’s Practical Organic Chemistry, 5th Edition. The nitrovaniline is reactive towards amine and forming 4-{(E)-[(4-aryl)imine]methyl}-2-methoxy-6-nitrophenol [4a-g]. The final compounds 4-{(E)-[(4-aryl)imine]methyl}- 2-methoxy-6-nitrophenol [4a-g] along with starting impurities are subjected to HPLC analysis.