Hydrochloric Acid → 1-(5-chloro-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine

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To a solution of (5-chloro-2-methylphenyl)hydrazine hydrochloride (1.49 g, 7.72 mmol, 1 eq) in 8 mL ethanol was added hydrogen chloride (4.0 mL of a 5 M aqueous solution, 20 mmol, 2 eq) and 3-aminocrotonitrile (0.664 g, 8.09 mmol, 1.05 eq). The reaction mixture was stirred at 80° C. for 16 hours and then brought to neutral pH with saturated aqueous sodium bicarbonate. The resulting solution was extracted twice with dichloromethane, and the combined extracts were dried over magnesium sulfate and concentrated to give 1-(5-chloro-2-methylphenyl)-3-methyl-1H-pyrazol-5-amine, which was carried forward without further purification. LCMS (ESI) m+H=222.2; 1H NMR (400 MHz, DMSO-d6) δ: 7.39 (d, 1H), 7.37 (d, 1H), 7.25 (s, 1H), 5.22 (s, 1H), 5.00 (s, 2H), 2.04 (overlapping s and s, 6H).

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