Nucleophilic Substitution Reactions of 4-Alkoxynaphthal-N-methylimide

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It was found that 4-substituted naphthal-N-methylimides were obtained by nucleophilic substitution of 4-alkoxynaphthal-N-methylimide. For example, 4-methoxy derivative was converted into 4-ethoxy derivative in almost quantitative yield by refluxing in ethanol containing sodium ethylate. As nucleophilic reagents, 11 alcohols, 4 amides (or imide), n-butylamine, phenol and sodium hydroxide were examined.In most cases, the corresponding 4-substituted derivatives were obtained in high yields, but the reaction with t-butanol, phenol and succinimide resulted in recovery of the starting 4-methoxy derivative. With benzyl alcohol and p-toluenesulfonamide, yields of the corresponding 4-substituted derivative were relatively low (55% and 41%, respectively).