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Paper | Regular issue | Vol 38, No. 6, 1994, pp.1317-1331
Published online, 1st January, 1970
DOI: 10.3987/COM-94-6683
Synthesis and Amination of 4-Chloro-3-quinolinesulfonyl Chloride

Andrzej Maslankiewicz* and Leszek Skrzypek

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

Abstract

Chlorinolysis of 4-chloro-3-benzylthioquinoline (2) or thioquinanthrene (1) using chlorine gas in the presence of water gave 4-chloro-3-quinolinesulfonyl chloride (3). Amination of (3) performed in ether led to 4-chloro-3-quinolinesulfonamides (4). Reactions of compound (3) with an excess of primary or secondary amine in two phase (water/toluene or benzene) system gave 4-(substituted amino)-3-quinolinesulfonamides (5) with two identical amine rests. While 4-chloro-3-quinolinesulfonamides (4) were aminated with an excess of amine into aminosulfonamides (5) with two identical or two various amine rests.