Iodine → N-(4-(aminomethyl)-3-chlorophenyl)methanesulfonamide

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In a three-neck round-bottom flask containing a 0° C. solution of LiAlH4 (2M in THF) (26.0 mL, 52.0 mmol) was added iodine (6.60 g, 26.0 mmol) in THF (20 mL) dropwise under N2. After addition, the mixture was stirred for 30 min at 0° C. N-(3-chloro-4-cyanophenyl)methanesulfonamide (4 g, 17.34 mmol) in THF (20 mL) was then added dropwise. After addition, the reaction mixture was warmed to room temperature and stirred for 1 h, during which time precipitate crashed out of the solution. The reaction mixture was filtered, and the cake washed with cold THF. The cake was carefully transferred to a beaker which contained 60 mL of THF. The mixture was acidified to pH=2 with 6N HCl with constant stirring at 0° C. The layers were separated and the aqueous layer was washed with DCM (30 mL). The aqueous layer was concentrated by rotary evaporation. The resulting solids were washed with cold MeOH to give a yellow solid. The mother liquid was subjected to the same workup (2×). The combined crops were collected and dried to give the title compound as the HCl salt (4.2 g, 89%). MS (ES+): m/e 234.7 [M+H]+.

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