Hydrochloric Acid → HCID 29548813, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-nitro-N-(pyridin-4-ylmethyl)-benzenesulfonamide [CAS No. 332942-34-4, commercially available] (1.23 g, 4.2 mmol), sodium dithionite (3.09 g, 15.1 mmol), water (10 ml) and 2 methoxyethanol (10 ml) was stirred at 100° C. for 2 h, additional water (7 ml) was added at 70° C. and subsequently HCl (37%, 7 ml) was added over a period of 10 min (SO2 evolution). The reaction mixture was stirred at 70° C. for 20 min, poured into ice/water (50 ml) and sodium carbonate was added until the solution proofed to be basic. The solution was extracted with ethyl acetate/MeOH 9:1 (3×75 ml), the combined organic layers washed with brine (80 ml), dried (MgSO4) and evaporated. The crude product was further purified by column chromatography on silica gel (MeOH/ethyl acetate 1:9) to yield the title compound (0.8 g, 72%) as a light yellow solid. MS (ISP) 261.9 [(M−H)−]; m.p. 139° C.

Provenance & Evidence