5-Chloro-2-methylaniline → (5-Chloro-2-methylphenyl)hydrazine hydrochloride

Beteiligte Stoffe

Reaktionsschritte

To an ice-cooled suspension of 5-chloro-2-methylaniline (1.4362 g, 10.143 mmol, 1.00 equiv) in water (10 mL) was added concentrated hydrochloric acid (10 mL). To this reaction mixture was added dropwise a solution of sodium nitrite (0.791 g, 11.5 mmol, 1.13 equiv) in water (5 mL) at 0° C. After 2 hours, the reaction mixture was slowly added to a stirring ice-cooled solution of tin chloride dihydrate (5.88 g, 25.8 mmol, 2.55 equiv) in concentrated hydrochloric acid (8 mL). Water was added as needed to maintain the stirring while solids formed. The reaction was kept at 0° C. for 45 minutes. The white solids were filtered and rinsed with diethyl ether (2×50 mL). The solids were dried under vacuum to provide 1.49 g (76%) of (5-chloro-2-methylphenyl)hydrazine hydrochloride. 1H NMR (400 MHz, DMSO-d6) δ: 10.08 (s, 3H), 7.98 (s, 1H), 7.13 (d, 1H), 6.97 (s, 1H), 6.91 (d, 1H), 2.14 (s, 3H).

Herkunft & Nachweise