Date of Award
Master of Science
The oxidation of 4-methyl quinoline presents a very interesting problem if viewed theoretically. From its formula one can predict the possibility of at least five acids resulting from the oxidation and possibly more depending upon the stability of the rings involved.
The resonance energy of the pyridine ring as compared with the benzene ring (17) and the relative stability of the methyl group suggest that oxidation would occur first at the methyl group, the benzene ring would then be attacked and the pyridine nucleus would be subject to attack last. Quinoline-4 carboxylic acid should theoretically be the first acidic product formed. Meuller (14) inferred that the oxidation of 4-methyl quinoline with sulfuric acid using a Selenium catalyst results in the production of a pyridine carboxylic acid. Weidel (23) stated that other products are formed in the oxidation of quinolepidene.
Our laboratory had need of quinoline-4 carboxylic acid and could not secure it from commercial sources. For this reason we proceeded to oxidize 4-methyl quinoline.
A search of the literature revealed interesting work done by Weidel (23). This worker oxidized quinolepidene with chromic acid. These experiments and those done later by Doebner and Miller (6, 7) form the basis of the present experiments.
E. E. O'Banion
Prairie View A&M College
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Date of Digitization
John B Coleman Library
City of Publication
Pollard, C. J. (1952). The Catalytic Liquid-Phase Oxidation of 4-Methyl Quinoline to Quinoline-4 Carboxylic Acid. Retrieved from https://digitalcommons.pvamu.edu/pvamu-theses/1304