Synthesis of a Hydrophilic Naphthalimidedioxime

Imidedioximes are formed in hydroxylamine-treated polyacrylonitrile adsorbents used in the extraction of uranium from seawater. Although known to be a good uranophile, the glutarimidedioxime model compound 1 is rapidly hydrolyzed under acidic conditions used to elute metals from the adsorbent. This work reports the synthesis of a hydrophilic naphthalimidedioxime derivative 14, which is stable under acidic elution conditions. The synthesis starts from simple acenaphthenequinone 7 and converts it to a functional group dense imidedioxime 14 in 7 steps.