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YELLOW CRYSTALLINE POWDER

3-Nitrophenylhydrazine Hydrochloride acts as a reagent in the preparation of isosteviol-fused pyrazolines and pyrazoles as potential anticancer agents, preparation of pyrazolobenzothiazines as inhibitors of hepatitis C virus replication.

Example 28: Synthesis of 3-methyl-1H-indol-6-amine 1. 3-Nitroaniline (27.6 g, 0.2 mol) was dissolved in a mixed solution of water (40 mL) and 37% hydrochloric acid (40 mL). 2. A solution of sodium nitrite (NaNO2, 13.8 g, 0.2 mol) in water (60 mL) was slowly added to the above solution at 0 °C. 3. Subsequently, a 37% hydrochloric acid (100 mL) solution of tin chloride dihydrate (SnCl2-2H2O, 135.5 g, 0.6 mol) was added, maintaining the reaction temperature at 0 °C. 4. After continuous stirring of the reaction mixture at 0 °C for 0.5 h, the insoluble solid was separated by filtration and washed with cold water to afford (3-nitrophenyl)hydrazine hydrochloride (27.6 g, 73% yield). Example 49: Synthesis of 6-amino-1H-indole-2-carbonitrile 1. 3-Nitroaniline (28 g, 0.20 mol) was dissolved in a mixture of water (40 mL) and 37% hydrochloric acid (40 mL). 2. A solution of sodium nitrite (NaNO2, 14 g, 0.20 mol) in water (60 mL) was slowly added to the above solution at 0 °C. 3. Subsequently, a 37% hydrochloric acid (100 mL) solution of tin chloride dihydrate (SnCl2-2H2O, 140 g, 0.60 mol) was added, maintaining the reaction temperature at 0 °C. 4. After continuous stirring of the reaction mixture at 0 °C for 0.5 h, the insoluble solid was separated by filtration and washed with cold water to afford (3-nitrophenyl)hydrazine hydrochloride (28 g, 73% yield).

[1] Patent: US2007/244159, 2007, A1. Location in patent: Page/Page column 110-111; 138
[2] Patent: US2012/309758, 2012, A1. Location in patent: Page/Page column 67
[3] Patent: US2015/231142, 2015, A1. Location in patent: Paragraph 0397; 1632; 1744
[4] Organic Preparations and Procedures International, 1991, vol. 23, # 3, p. 357 - 364
[5] Journal of Agricultural and Food Chemistry, 2014, vol. 62, # 2, p. 381 - 390