Abstract: Current undergraduate organic chemistry experiments predominantly focus on simple single-step reactions, with limited exposure to one-pot tandem reactions. This experiment employs cost-effective and readily available starting materials, 3-methyl-2-indolinone and 2-chloro-5-nitroacetophenone, to demonstrate a tandem process combining aromatic nucleophilic substitution (S_NAr) with Aldol condensation. The methodology enables the synthesis of 2,3-fused indoline derivatives featuring a quaternary carbon center. The experiment incorporates substantial theoretical concepts while maintaining operational simplicity, reaction stability, and excellent reproducibility.

Key words: Tandem cyclisation reaction, S_NAr reaction, Aldol condensation, Quaternary carbon-containing fused indoline