Arsonnic and Stibonic Acids derived from QuinoLine, etc. Part I . 433 99. Arsonic and Stibonic A c i d s derived from Quinoline and Acridine. Part I . By (Miss) MARY M. BARNETT, ARCHIBALD H. C. P. GILLIESON, and WILLIAM 0. KERMACK. FOR the preparation of 3-aminoacridone (I, R = NH,) in moderately large quantities the following two methods were found suitable : (1) 4'-Nitrodiphenylamine-2-carboxylic acid (Goldberg, Ber., 1906, 39, 1691) is reduced by ferrous sulphate and ammonia, and the resulting 4'-arninodiphenylamine-2-carboxylic acid heated with 96 yo sulphuric acid at 100" ( U h a n n and Bader, Annalen, 1907, 355, 335). (2) Condensation of o-bromobenzoic acid and P-aminoacetanilide in amyl-alcoholic solution in presence of potassium carbonate and copper powder yields 4'-acetamidodi~henylamine-2-carboxylic acid, from which 3-aminoacridone is readily obtained by treatment with 96% H,SO, at 100". 3-Aminoacridone is converted into acridone-3-arsonic acid (I, R = AsO,H,) by the Bart reaction under appropriate conditions, and into acridone-3-stibonic acid (I, R = SbO,H,) under the conditions described by Morgan and Cook (J., 1930, 743). * Wieland and Wiedersheim do not record a m. p. for this acid; our product did not depress the m. p. of a specimen, m. p. 186", very kindly supplied by Professor Wieland.
EDINBURGH.[Received, J a ti uary 2 9 th, 1 93 4 .]