Hydrochloric Acid → 3-(Hydroxymethyl)benzene-1-sulfonamide

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Reaction Steps

3-(Aminosulfonyl)benzoic acid (2.18 g) was stirred with ice-water cooling and under nitrogen while borane-THF complex (32.5 ml) was added dropwise over 15 min. After 2 h at 22° further borane-THF complex (16 ml) was added. After a further 2 h the mixture was cooled with ice-water and methanol (40 ml) was added dropwise. After 15 min 2M hydrochloric acid (90 ml) was added and the mixture was left to stand at 21° overnight. The solution was extracted 3 times with ethyl acetate and the organic layers were combined and washed twice with brine, dried (MgSO4) and concentrated. This solution was loaded onto a column of silica gel (200 g) and the column was run with ethyl acetate and then 10% methanol in ethyl acetate to give the title compound (1.595 g), LCMS RT=0.83 min.

Provenance & Evidence