Benzoic acid, 3-(aminosulfonyl)-, methyl ester → 3-(Hydroxymethyl)benzene-1-sulfonamide

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To a solution of methyl 3-(aminosulfonyl)benzoate (520 mg, 2.4 mmol) in THF/EtOH (24 mL, 1:1), CaCl2 (533 mg, 4.8 mmol) and NaBH4 (363 mg, 9.6 mmol) were added in one portion respectively. The reaction mixture was stirred at room temperature for 6 hours, and then quenched with water. 1 M aqueous citric acid (8 mL) was added to the mixture and extracted with EtOAc (3×100 mL). The extracts were combined, washed with brine, and dried (Na2SO4). The solvent was evaporated to afford the product (307 mg, 68%) as a white solid. MS (ES+) m/z 210 [M+Na]+.

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