Uses
4-Chloro-5-trifluoromethyl-o-phenylenediamine has application in dietary supplements, pharmaceutical or cosmeticeuticals.
Synthesis
General procedure for the synthesis of 2-chloro-4,5-diaminotrifluoromethylbenzene from 5-chloro-2-nitro-4-(trifluoromethyl)aniline: 5-chloro-2-nitro-4-(trifluoromethyl)aniline (2 g, 8.31 mmol) was dissolved in a solvent mixture of EtOH:H2O (5:1, 10 mL) at room temperature. Subsequently, SnCl2 (4.73 g, 24.9 mmol) was added to the solution. The reaction mixture was stirred at 80°C for 3 hours. The progress of the reaction was monitored by thin layer chromatography (TLC) and after confirming the completion of the reaction, the reaction mixture was filtered through a bed of diatomaceous earth and the filtrate was concentrated under reduced pressure to afford 4-chloro-5-(trifluoromethyl)benzene-1,2-diamine as a yellow semi-solid product. Yield: 1.7 g, 97% yield. The product was characterized by 1H NMR (400 MHz, DMSO-d6): δ 6.95 (s,1H), 6.88 (s,1H), 4.68-5.08 (bs,4H). Mass spectrometry (ESI-) analysis showed m/z 209.15 [M-H]-.
References
[1] Patent: WO2018/37223, 2018, A1. Location in patent: Page/Page column 118; 119
[2] Journal of Medicinal Chemistry, 1995, vol. 38, # 22, p. 4367 - 4379
[3] Patent: WO2004/35549, 2004, A1. Location in patent: Page 105
[4] Patent: WO2008/56150, 2008, A1. Location in patent: Page/Page column 182
