The synthesis of alkylamino-N-alkylnaphthalic-1,8-imides from 2- and 4-nitronaphthalic anhydrides by nitro group displacement

4-Alkylamino-N-alkylnaphthalic-1,8-imides and 2-alkylamino isomers have been synthesised by the reaction of 4-nitro- and 2-nitronaphthalic anhydrides respectively with primary amines in aprotic solvents in which reaction the nitro group in 3-nitronaphthalic anhydride is unreactive. Unsymmetrical compounds in the 2- and 4-series are derived from either the appropriate 4-nitro-N-alkylnaphthalic-1,8-imide or for 4-dialkylamino compounds from 4-nitronaphthalic anhydride by reaction with a secondary amine and then the 4-dialkylaminonaphthalic anhydride with a primary amine.