The Reaction of Acridine with Sodium Amide without Solvent

Abstract

A mixture of acridine and sodium amide in the equimolar ratio was heated without solvent at 130°C or more; 9-aminoacridine was then obtained in 31.0% yield during the melting of the mixture. The reaction mixture was coagulated a few minutes after the reaction started, and 9-aminoacridine finally produced.9, 9', 10, 10'-Tetrahydro-9, 9'-biacridine as another product was yielded slowly during both the melting and solid condition of the reaction mixture. The important characteristic of this reaction was that acridine readily underwent amination as the Chichibabin reaction; at the same time, the acridine was reduced by the hydrogen produced during the reaction. Therefore, 9-aminoacridine and 9, 9', 10, 10'-tetrahydro-9, 9'-biacridine were obtained in this reaction when simply heated without solvent; this Chichibabin reaction was a novel reaction of acridine.