Synthesis and characterization of new fatty Schiff base ethers of 4-((pyridin-3-ylmethylimino)methyl)phenol

Abstract

A series of ten new Schiff base ethers were synthesized by etherification of Schiff base-{4-(pyridine-3-methylimino) methyl phenol} with fatty alkyl bromides of different chain lengths (C₄-C₁₈) in the presence of base with 80-85% isolated yields. All the synthesized Schiff base ethers (2a-j) were characterized by FT-IR, ¹H NMR, ¹³C NMR and Mass spectral studies. Presence of a characteristic peak for ether linkage, C-O at 1039 cm^-1 in IR spectra; a triplet around 7.67 ppm in ¹H NMR and a characteristic peak around 69.7 in case of ¹³C NMR further confirmed the structures of Schiff base ethers. The structure of all the compounds were further confirmed by their characteristic molecular ion peaks in ESI-MS.