Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
A Kinetic Study of Cyclodehydration of β-(p-Toluidino) acrolein. II. Sulfonation of the Aromatic Ring as a Side Reaction of Cyclodehydration in Sulfuric Acid
SHINZO TAMURAREIKO TODORIKI
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1980 Volume 28 Issue 11 Pages 3395-3400

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Abstract
Sulfonation of the benzene ring of 3-(p-toluidino)-1-oxo-2-propene-2-sulfonic acid (III) (6.11×10-5M) in 99.4% sulfuric acid at 25° was observed by following the UV spectral change of the solution. In a 9.51×10-1M solution in 99.4% sulfuric acid, however, the bulk of III remained unchanged, and on dilution with 93.8% sulfuric acid, 6-methyl-quinoline (II) was formed. Sodium 4-(3-oxo-1-propenylamino) benzenesulfonate (V), sodium 4-(3-oxo-1-propenylamino)-3-methylbenzenesulfonate (VI) and sodium 2-(3-oxo-1-propenylamino)-5-methyl-benzenesulfonate (VII) were synthesized in connection with this investigation.
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© The Pharmaceutical Society of Japan
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