Abstract: Reductive amination is a practical method for converting carbonyl compounds to amines. Using this reaction as an example, we introduce a comprehensive organic chemistry experiment designed for senior undergraduates: the reductive amination of isophthalaldehyde with silane to synthesize m-xylylenediamine. In this reaction, tert-butyl carbamate (BocNH₂) serves as the nitrogen source, and triethylsilane (Et₃SiH) acts as the reducing agent, with trifluoroacetic acid as the catalyst. Isophthalaldehyde undergoes reductive amination to produce Boc-protected m-xylylenediamine, which is subsequently deprotected to yield m-xylylenediamine hydrochloride. The final product, m-xylylenediamine, is obtained by treating the hydrochloride salt with sodium hydroxide. The experimental procedure includes techniques such as extraction, vacuum distillation, drying, recrystallization, and melting point determination, along with analytical methods like thin-layer chromatography (TLC), infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy. This synthetic route is well-suited for laboratory synthesis, providing high yields and easy purification of the product. The experiment enhances students’ skills in organic synthesis and deepens their understanding and application of spectroscopic techniques.

Key words: Reductive amination, m-Xylylenediamine, Isophthalaldehyde, Amine