GB611745A - Improvements in or relating to the production of phenanthridine compounds - Google Patents

Abstract

A 9-phenylphenanthridine, which contains one or more nitro groups in the benzene nuclei, is made by heating a 2-aminodiphenyl having the 21- or 61-position free, with benzotrichloride or benzotribromide, in an ionizing solvent medium and in presence as catalyst of aluminium chloride, stannic chloride, ferric chloride, zinc chloride, bismuth trichloride, bismuth oxychloride, or zirconium chloride. The reaction is continued until evolution of hydrogen halide has ceased, and the temperature is kept above 195 DEG C. throughout the greater part of the reaction. The products may be converted to quaternary salts. Intermediate products stated to have been isolated are a benzamidine and its hydrochloride, and the benzoyliminochloride or bromide. Nitrobenzene and nitrotoluene are specified as solvents, though a nitroparaffin of lower boiling point may be used for the first stage. In general, the trihalide is employed in slight excess, the catalyst in a proportion of about .1 mol. per mol. of aminodiphenyl, and the catalyst and trihalide are added simultaneously or in succession to a solution of the aminodiphenyl in the solvent. Quaternation may be effected by adding the quaternating agent to the crude reaction mixture containing the phenanthridine. In examples, benzotrichloride is reacted in nitrobenzene in presence of stannic chloride with (1) 4.41-dinitro-2-aminodiphenyl, (2) 41-nitro-2-aminodiphenyl, (3) 5-nitro-2-aminodiphenyl. Also in examples, the stannic chloride is replaced in (1) by aluminium, zinc and bismuth chlorides, and the reaction mixture may be treated with dimethyl sulphate to give the methyl phenanthridinium sulphate or converted to the phenanthridinium chloride. Specifications 372,859 and 520,273 are referred to.