Citric Acid → HCID 178449961, compound

Participants

Reaction Steps

A solution of 5-bromopyridin-2-ol (1.00 g, 5.75 mmol) in chlorosulfonic acid (15.0 mL, 224 mmol) was heated to 150° C. for 14 h. The reaction mixture was added dropwise to tert-butyl amine (25 mL) in THF (25 mL) at 0° C. and was evaporated under reduced pressure to give a brown residue. The residue was dissolved in water (100 mL) and acidified with saturated citric acid solution (pH=6) and extracted with ethyl acetate (2×100 mL). The combined organic layers were dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to a residue which was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 24 g, 60% EtOAc/hexanes) to obtain 5-bromo-N-(tert-butyl)-2-hydroxypyridine-3-sulfonamide (0.260 g, 14.6%). LCMS Condition B-24: retention time 1.10 min, [M+2]=309.0.

Provenance & Evidence