Date on Master's Thesis/Doctoral Dissertation
Jensen and Friedrich have outlined new methods for the preparation of acridine compounds. They have shown that the treatment of o-aminobensaldehyde with the halogen derivatives of nitrobenzene and with the corresponding derivatives of toluene would yield the corresponding diphenylamine derivatives. These diphenylamine derivatives split off water very easily to form acridine compounds. By this method they have prepared the 1(9)-nitro and 3(7)-nitroacridine, and the 1(9)-methyl and 3(7)-methylacridine. The general application of the reaction used in preparing these compounds has been examined, and it has been found that the reaction can be extended in two ways. Halogen derivatives of benzene compounds, other than those mentioned, can be used, or the aminobenzaldehyde can be replaced by o-amino phenylketones. The halogen derivatives of phenol were chosen first for the following reason. K. Motsumura has described the preparation of 1(9)-hydroxyacridine by reduction of the corresponding acridine compound in boiling amyl alcohol with sodium. These results seemed open to question because it was believed that the dihydroacridine should be obtained, since acridine itself will give dihydroacridine under the conditions stated. As the products obtained from the phenol are identical with those of the Japanese chemist, no hydrogenation of the acridine ring occurred during the reduction. In this work the free phenols could not be used as the hydroxyl group itself reacted. For this reason the methyl and ethyl ethers were employed. Next the o-aminobenzaldehyde was replaced by o-aminiophenylketones. This reaction should lead to 5-position acridine derivatives according to the following scheme.
Rethwisch, Francis Bratten, "The preparation of hydroxy-acridines and different 5-position acridine derivatives." (1928). Electronic Theses and Dissertations. Paper 1198.