GB641569A - 4-acylamino-1, 8-naphthalimides and their preparation - Google Patents

Abstract

4-Acylamino-1.8-naphthalimides are made by condensing 4-nitronaphthalic acid anhydride with ammonia or an aliphatic or aromatic primary amine in an organic solvent, reducing the nitro group and acylating with the anhydride or acyl chloride of an aliphatic or aromatic carboxylic acid. The imido group may be unsubstituted or may be substituted by alkyl, hydroxyalkyl, carboxyalkyl, cycloalkyl, aralkyl, aryl, carboxyaryl, alkoxyaryl, hydroxyaryl (e.g. salicyl), and the acyl radical may be formyl, carbamyl, the radical of a fatty acid which may be substituted by hydroxy, amino, alkoxy or aryloxy, or a cycloaliphatic acid, or an aromatic acid which may be substituted by hydroxy, amino, or alkoxy, and the amines and acylating agents may be chosen accordingly. A list of illustrative products is given and in examples 4-nitronaphthalic anhydride is condensed with the following amines followed by reduction and acetylation: (1) n-butylamine; (2) n-octylamine; (3) n-tetradecylamine; (4) n-octadecylamine; (5) benzylamine. Also in examples, 4-amino - N - n - butyl - 1.8 - naphthalimide (obtained as under (1) above) is (6) benzoylated; or (7) hexahydrobenzoylated; and (8) 4-amino - N - n - tetradecyl - 1.8 - naphthalimide is benzoylated. The products dissolve in organic solvents with a bluish fluorescence, and give fluorescent dyeings.