GB346359A - The manufacture and production of halogenated products of anthraquinone derivatives - Google Patents

Abstract

Halogenated anthraquinone acridones; halogenated anthraquinonyl-N-isatins.-a -Anthraquinonyl-N-isatins or alkyl or halogen derivatives thereof are treated with halogen or halogenating agents whereby halogenated products are obtained which, in some cases, are anthraquinone acridones. Halogenation may be carried out in the presence or absence of organic or inorganic solvents or diluents and of halogen transferrers. Those products which are halogenated isatin derivatives may be treated with acid or alkaline condensing agents such as aluminium chloride, sulphuric acid or caustic alkalies to effect acridone ring-closure. In examples (1) 1-N-isatylanthraquinone is treated with sulphuryl chloride in nitrobenzene and in presence of iodine to give a 1-N-dichlorisatylanthraquinone which is converted in the vat to a dichloranthraquinone-2-1-benzacridone (dyes red shades); if bromine is used instead of sulphuryl chloride and iron is also present, a bromanthraquinone-2-1-benzacridone dyeing blue-red shades is obtained; treatment with chlorine and then with bromine in an aluminium sodium chloride melt yields a chlorobromoanthraquinone-2-1-benzacridone (dyes blue-red shades): (2) 1-N-methylisatylanthraquinone (derived from 1-p-toluidoanthraquinone) is treated with chlorine in an aluminium sodium chloride melt (or ferric chloride) to give a chloranthraquinone-2-1-methylbenzacridone (dyes red shades): (3) 1,5-di-N-isatylanthraquinone is treated with bromine in nitrobenzene and in presence of iodine and iron to give a bromanthraquinone-2-1 : 6-5-dibenzacridone (dyes reddish-blue shades): (4) 1-N-b -naphthisatyl anthraquinone is treated with bromine in nitrobenzene and in presence of sulphur and iodine to give a brominated anthraquinone-2-1-naphthacridone (dyes yellow-red shades); the same product is obtained by treating the 1-b -naphthylaminoanthraquinone with oxalyl chloride and brominating the reaction mass as above: (5) 1-N-chlorisatylanthraquinone (derived from 1-m-chloranilidoanthraquinone) is treated with bromine in nitrobenzene in presence of iodine to give a chlorobromoanthraquinone-2-1-benzacridone (dyes blue-red shades); treatment with chlorine in trichlorbenzene in presence of iodine gives a chlorinated 1-N-isatylanthraquinone which on vatting is transformed to an acridone containing two or three atoms of chlorine; by the bromination as above of the 1-N-chlorisatylanthraquinones derived from 1-o-and 1-p-chloranilidoanthraquinone similar chlorobromoacridone derivatives are obtained. The 1-N-isatylanthraquinones may be prepared by the action of oxalyl chloride on an arylaminoanthraquinone, preferably in the presence of condensing agents such as aluminium chloride, or by reacting halogenated anthraquinones with isatins.