GB680496A - 9-propylamino-5-arylaminobenzo[ª‡]phenoxazines - Google Patents

Abstract

p-Nitrosoanilines substituted at the nitrogen atom by an ethyl and a propyl group, a propyl and an isopropyl group, or a butyl and a propyl group are made by the reaction of sodium nitrite with the corresponding amine in presence of hydrochloric acid. 2-Nitroso-5-di-n-propylamino phenol is obtained similarly from the dipropylated aminophenol.ALSO:The invention comprises benzophenoxazine dyes which, in the form of their free bases, have the formula <FORM:0680496/IV (c)/1> where R1 is propyl, R2 is alkyl of 2-4 carbon atoms, and R3 is a monocyclic aromatic radical, and their addition salts with acids. These compounds are stated to be effective against tubercle bacilli and are prepared by heating under ring-closing conditions compounds of the formul <FORM:0680496/IV (c)/2> and <FORM:0680496/IV (c)/3> where X and Y are different and are H or OH, and Z is H when Y is OH, and NH-aryl when Y is H. When Y is OH, the product first obtained is heated with a primary amine of the benzene series. In examples: (1) N,N - di - n - propyl - 4 - nitroso - aniline hydrochloride is heated with b -naphthol in presence of alcohol and zinc chloride, and the 9 - di - n - propylaminobenzo - [a] - phenoxazonium nitrate so obtained is heated with alcohol and aniline, p-toluidine, p-ethylaniline, m-toluidine, o-toluidine, 2,4-xylidine, or p-isopropylaniline; (2) 9-ethylpropylaminobenzo-[a]-phenoxazonium nitrate hydrochloride is similarly prepared and heated with aniline or p-toluidine; (3) 9-n-propylisopropylamino-benzo-[a]-phenoxazonium nitrate is similarly prepared and reacted with p-toluidine; (4) 9 - butylpropylaminobenzo - [a] - phenoxazonium nitrate is similarly prepared and reacted with aniline, p-toluidine, p-chloraniline, or o-toluidine. Also in examples, (5) 2-nitroso-5-di-n-propylamino-phenol is heated with N-phenyl - a - naphthylamine to give 5 - phenylamino - 9 - di - n - propylaminobenzo - [a]-phenoxazine base. Also in examples, 5-(4-methylphenylamino) - 9 - di - n - propylaminobenzo - [a] - phenoxazine base, and the corresponding 5 - phenylamino - 9 - butyl-propylamino body are obtained from the corresponding nitrates and aqueous ammonia.