Ammonium Hydroxide → 6-chloropyridine-3-sulfonamide

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Reaction Steps

6-chloropyridine-3-sulfonyl chloride (4.1 g, 19.3 mmol) was stirred in ammonium hydroxide (30 mL) at room temperature for 2 hr. The reaction mixture was diluted with EtOAc (150 mL) and any insoluble material filtered. The filtrate was transferred to a separatory funnel and the phases were separated. The aqueous phase was further extracted with EtOAc (1×15 mL). The combined EtOAc extractions were washed with H2O (1×50 mL), saturated NaCl (1×50 mL), dried (Na2SO4), and concentrated in vacuo to give 6-chloropyridine-3-sulfonamide (2.58 g, 69%). MS (EI) for C5H3Cl2NO2S: 190.9 (MH−).

Provenance & Evidence