Stannous Chloride → 3-Chloro-4-(4-methylpiperazin-1-yl)aniline

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To a stirred solution of 1-(2-chloro-4-nitrophenyl)-4-methylpiperazine (2.43 g, 9.5 mmol) in 2N HCl (35 mL) at RT was added tin (II) chloride (7.2 g, 38 mmol). After 1 h, the solids were collected by filtration and dissolved in aqueous 1 N NaOH (300 mL). The aqueous solution was extracted with ethyl acetate (3×50 mL). The combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, filtered, and evaporated to afford the title compound (2.02 g, 95%).

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