Uses
4-(1,2,4-Triazol-1-yl)aniline is used in the preparation of pyrimidine compounds that inhibit anaplastic lymphoma kinase and are useful in the treatment of cancers.
Synthesis
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.
References
[1] Chemical and Pharmaceutical Bulletin, 2000, vol. 48, # 12, p. 1935 - 1946
[2] Patent: US2015/336982, 2015, A1. Location in patent: Paragraph 0160; 0162
[3] Applied Spectroscopy, 1995, vol. 49, # 8, p. 1111 - 1119
[4] Patent: US2005/143384, 2005, A1. Location in patent: Page/Page column 23-24
[5] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2012, vol. 51, # 5, p. 731 - 738
