The constitution of hydroxysulphapyridine and synthesis of 2-aminohydroxypyridines

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Abstract
An attempt was made to identify the aminohydroxypyridine moiety of hydroxysulfapyridine, the metabolite of sulfapyridine in the rabbit. 2-Amino-6-hydroxy-and 2-amino-3-hydroxypyridines were synthesized and shown to differ from the biosynthetic compound. Unsuccessful attempts were made to prepare 2-amino-4-hydroxy- and 2-amino-5-hydroxy-pyridine, although evidence was obtained that the latter is a minor product in the prepn. of the 2,3-isomer, Claims by earlier workers to have prepared the 2,5-isomer were shown to refer to the 2,3-isomer. Evidence was obtained that the biosynthetic product is 2-amino-5-hydroxypyridine and hence hydro-sulfapyridine is 2-(p-aminobenzenesulfon-amido)-5-hydroxypyridine.