Abstract
The degradation products from acid and base hydrolysis of methaqualone, 2-methyl-3-o-tolyl-4(3H)-quinazolinone, were isolated and identified by combined methods using liquid–liquid extraction, TLC, GLC, and IR, UV, and visible spectroscopy. Examination of the degradation products resulting from the hydrolysis of methaqualone revealed that, in boiling acidic or basic media, anthranilic acid, o-toluidine, and acetic acid were the major degradation components. The formation of the other degradation products, N-acetylanthranilic acid and 2-aminobenzo-o-toluidide, was acid–base strength dependent. The degradation of methaqualone in basic or acidic media followed different reaction pathways, but the primary decomposition was due to hydrolytic cleavage. The relationship between the degradation product, 2-aminobenzo-o-toluidide, and 2-nitrobenzo-o-toluidide, a metabolite of methaqualone in humans, is discussed.
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