4-Nitrophenylhydrazine hydrochloride synthesis

Yield:636-99-7 39%

Reaction Conditions:

Stage #1:4-nitro-aniline with hydrogenchloride;sodium nitrite in water at 0; for 1 h;
Stage #2: with hydrogenchloride;tin(ll) chloride in water at 0; for 2 h;

Steps:

4.1.17 (4-Nitrophenyl)hydrazine, hydrochloride salt (26)
p-Nitroaniline (25) (1.47 g, 10.6 mmol) was dissolved in concd HCl (2 mL) and cooled to 0 °C. A solution of sodium nitrite (717 mg, 10.4 mmol) in ice-cooled water (4 mL) was added drop wise to above reaction mixture and stirred for 1 h in an ice bath. Ice-cooled solution of stannous chloride (4.7 g, 20.8 mmol) in concd HCl (2 mL) was added slowly to above diazonium reaction mixture. The reaction was stirred at 0 °C for 2 h. A yellow-orange precipitate was collected and washed thoroughly with ice-cold water until the filtrate pH was neutral. The precipitate was dried overnight under vacuum to give compound 26 (640 mg, 4.18 mmol, 39%); ¹H NMR (DMSO-d₆) δ 4.49 (s, 2H), 6.78 (d, J = 8.78 Hz, 2H), 7.98 (d, J = 9.29 Hz, 2H), 8.41 (s, 1H).

References:

Purohit, Meena K.;Chakka, Sai Kumar;Scovell, Iain;Neschadim, Anton;Bello, Angelica M.;Salum, Norue;Katsman, Yulia;Bareau, Madeleine C.;Branch, Donald R.;Kotra, Lakshmi P. [Bioorganic and Medicinal Chemistry,2014,vol. 22,# 9,p. 2739 - 2752]

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