4-(1,2,4-TRIAZOL-1-YL)ANILINE

6219-55-2

6523-49-5

1-(4-Nitrophenyl)-1H-1,2,4-triazole (3.0 g, 15.78 mmol) was used as a raw material and co-dissolved with ammonium chloride (2.1 g, 39.62 mmol) in 50% ethanol-water mixed solvent (60 mL). Zinc powder (2.6 g, 40 mmol) was then added and the reaction mixture was heated to reflux for 30 min. After completion of the reaction, it was cooled to room temperature, filtered to remove insoluble material and the filter cake was washed with ethanol (10 mL). The filtrates were combined and concentrated under reduced pressure to remove the solvent, the residue was diluted with water (100 mL) and extracted with ethyl acetate (100 mL x 3). The organic layer was dried with anhydrous sodium sulfate, filtered and concentrated under reduced pressure to afford 4-(1H-1,2,4-triazol-1-yl)aniline (1.1 g, yield: 81%) as a yellow solid, and the product could be used in the subsequent reaction without further purification. m/z = 161 [M + H]+ by LC-MS (ESI) analysis.