GENERAL METHODS: In a catalyzed reaction, Catalyst C1 (12 mg, 0.01 mmol), imidazole (1.0 mmol), 4-bromoaniline (1.0 mmol), NaOH (80 mg, 2.0 mmol), and dimethyl sulfoxide (DMSO, 5 mL) were added to a sealed tube. The reaction mixture was stirred at 100 °C for 4 h and subsequently cooled to room temperature. After the reaction was completed, 5 mL of water was added and the mixture was extracted with ethyl acetate (5 mL x 3). The organic layers were combined, dried with anhydrous Na2SO4 and concentrated under reduced pressure to remove the solvent. Finally, the target product 4-(imidazol-1-yl)aniline was purified by silica gel column chromatography.
