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Paper | Regular issue | Vol 57, No. 11, 2002, pp.2035-2044
Published online, 1st January, 1970
DOI: 10.3987/COM-02-9562
The Preparation of the Stable Tautomers of 4-Mercapto-3-quinolinesulfonic and 1,4-Dihydro-4-thioxo-3-quinolinesulfonic Acids

Leszek Skrzypek* and Kinga Suwinska

*Department of Organic Chemistry, The Medical University of Silesia, Jagiellonska Str. 4, 41-200 Sosnowiec, Poland

Abstract

The reaction of 4-chloro-3-quinolinesulfonic acid (3) with sodium hydrosulfide gives the sodium salt of 1,4-dihydro-4-thioxo-3-quinolinesulfonic acid (4) and 4-mercapto-3-quinolinesulfonic acid (4b). The acidification of aqueous solution of the sodium salt of 4 results in 1,4-dihydro-4-thioxo-3-quinolinesulfonic acid (4a). It has been found that in the DMSO solution tautomer (4a) converts into tautomer (4b). The X-Ray analysis of tautomer (4a) indicates that it appeared in a form of betaine (4c).