Acridone studies. XIV. The selective demethylation of 2,3-Dimethoxy-10-methyl-9-oxoacridine-1,4-quinone by base

Abstract

The selective demethylation of 2,3-dimethoxy-10-methyl-9-oxoacridine- 1,4-quinone by sodium hydroxide has been studied by following the change in product composition with hydroxide concentration, by measuring the relative extent of exchange at C2 and C3 with sodium methoxide[T], and by following the kinetics of the reaction in alkali. Reaction pathways are proposed to rationalize the observation that the C2 methoxyl group is replaced more readily in dilute alkali or on warming, but the C 3 methoxyl group is replaced in more concentrated alkali.