Optimization of the Synthesis Parameters of
(E)-4-(Dimethylamino)-N-Benzylideneaniline
Shams Aghazade1 
, Almaz Huseynova1 , Nariman Aliyev1 ,
Pari Huseynova2* , Bahruz Mammadov3
Abstract. Schiff bases containing azomethine functional groups continue to attract considerable interest due to their structural diversity and broad applicability in coordination chemistry, organic synthesis, and functional material design. In the present study, (E)-4-(dimethylamino)-N-benzylideneaniline was synthesized through the condensation reaction of 4-dimethylaminobenzaldehyde with aniline in ethanol medium under mild acidic conditions. The influence of major synthesis parameters, including reaction temperature, reaction time, and catalyst amount, on product yield and crystallization behavior was systematically investigated. The reaction progress was visually monitored through changes in solution color and crystal formation. Experimental results demonstrated that the synthesis efficiency strongly depended on reaction conditions. Moderate temperatures promoted effective azomethine bond formation, whereas excessive heating reduced product quality and yield. The optimal synthesis conditions were determined to be 50 °C reaction temperature, 35 minutes reaction time, and the addition of two drops of acetic acid catalyst. Under these conditions, the target Schiff base was obtained as an intense yellow crystalline compound with high yield. The study confirms that mild reaction conditions provide an efficient and experimentally simple approach for the synthesis of conjugated azomethine derivatives.
Keywords: schiff base, azomethine, condensation reaction, synthesis optimization, dimethylaminobenzaldehyde, aniline