Abstract

Schiff bases (imines) are an important class of organic compounds formed by the condensation of primary amines with carbonyl compounds and are widely recognized for their structural versatility and broad biological relevance. In this study, a series of aromatic Schiff bases were synthesized via the condensation of 4-hydroxybenzaldehyde with aniline, 2,4-dimethylaniline and 2,4,6-trimethylaniline under reflux conditions in methanol. The reactions proceeded smoothly, affording the desired imines in moderate to good yields (56-73%). The synthesized compounds, namely 4-((phenylimino)methyl) phenol, 4-((2,4-dimethylphenylimino)methyl)phenol, and 4-((mesitylimino)methyl)phenol were isolated as crystalline solids and characterized comprehensively. Structural confirmation was achieved using melting point analysis, elemental analysis, 1H and 13C NMR spectroscopy, and mass spectrometry all of which were consistent with the proposed molecular structures. The influence of aromatic substitution on reaction yield and physicochemical properties was also observed. Given the well-documented pharmacological and functional significance of Schiff bases, these synthesized imines derivatives may serve as useful intermediates or scaffolds for future studies in medicinal chemistry and materials science..

Keywords:Schiff bases; Aniline; Aldehyde; Spectroscopy and biological activities