Hydrochloric Acid → HCID 86656449, compound

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Reaction Steps

To a solution of N-(4-acetyl-6-chloropyridin-3-yl)-4-nitro-N-(4-nitrophenylsulfonyl)benzenesulfonamide (1.0 equiv.) in 2:1 THF/MeOH (0.05 M) was added 1 M LiOH (aq.) (3.1 equiv). The resulting purple solution was stirred at rt for 15 hours, at which time 1 M HCl (3.1 equiv) was added. The volatiles were removed in vacuo and ethyl acetate (700 mL) and H2O (200 mL) were added. Upon separating the organic was washed with NaHCO3(sat.) (200 mL), with NaCl(sat.) (200 mL), dried over MgSO4, filtered and concentrated. Purification by column chromatography (50% ethyl acetate/hexanes with 0.1% AcOH, Rf=0.6) yielded N-(4-acetyl-6-chloropyridin-3-yl)-4-nitrobenzenesulfonamide (84%). LCMS (m/z): 356.0 (MH+); LC Rt=3.81 min. 1H NMR (CDCl3): δ 8.89 (s, 1H), 8.32 (m, 2H), 8.06 (m, 2H), 7.62 (s, 1H), 2.60 (s, 3H).

Provenance & Evidence