Uses
4-Tolylhydrazine Monohydrochloride has shown tumorigenic potential through studies. In addition, due to its hydrazine moiety, it has anti-cancer potential and is a compound from which derivatives are
made in the search of novel anticancer drugs.
Uses
4-Tolylhydrazine Monohydrochloride has shown tumorigenic potential through studies. In addition, due to its hydrazine moiety, it has anti-cancer potential and is a compound from which derivatives are made in the search of novel anticancer drugs.
Synthesis
General procedure for the synthesis of 4-methylphenylhydrazine hydrochloride from 4-methylaniline: 4-methylaniline (10.7 g, 0.1 mol) was mixed with dilute hydrochloric acid in a 200 ml round bottom flask. Sodium nitrite solution (30 ml, 7.3 g, 0.105 mol) was added slowly and dropwise to the above mixture. The reaction mixture was stirred for 1 hour and then filtered. The filtered clear liquid was added dropwise to 70 ml of aqueous solution containing sodium sulfite (37.8 g, 0.3 mol) and reacted at 80°C for about 1.5 hours. Subsequently, concentrated hydrochloric acid (25 ml, 0.3 mol) was added slowly and the reaction temperature was raised to 95°C and the reaction continued for about 2.5 hours. Upon completion of the reaction, the mixture was allowed to stand at room temperature overnight to precipitate 4-methylphenylhydrazine hydrochloride as a solid. After filtration and drying, 12.9 g of product was obtained in 90.0% yield.
References
[1] Patent: CN108623511, 2018, A. Location in patent: Paragraph 0021
[2] Patent: EP2157088, 2010, A1. Location in patent: Page/Page column 41-42
[3] Russian Chemical Bulletin, 2005, vol. 54, # 10, p. 2417 - 2424
[4] European Journal of Medicinal Chemistry, 2010, vol. 45, # 10, p. 4692 - 4696
[5] European Journal of Medicinal Chemistry, 2011, vol. 46, # 5, p. 1706 - 1712
