GB790203A - Improvements in and relating to naphthalene derivatives and the manufacture thereof - Google Patents

Abstract

The invention comprises naphthalene derivatives of the general formula: <FORM:0790203/IV (b)/1> in which X and Y each represent the grouping -CH2,NR5,CH2,O-, R5 being a straight or branched chain alkyl group having from one to eight carbon atoms or a cycloalkyl group having from five to seven carbon atoms in the ring; together with a process for their preparation by reacting the appropriate naphthalene 1,5-, 1,6- or 2,6-diol with formaldehyde and an amine RNH2, preferably in a solvent, e.g. methanol. In examples: (1) naphthalene-1,6-dol is added to cyclohexylamine and formalin in methanol at -5 DEG C. and the mixture left overnight, when 2,9 - dicyclohexyl - 1,2,3,4,7,8,9,10-octahydro - 2,9 - diaza - 4,7 - dioxachrysene separates and is recrystallized from ethanol or dioxan; similarly using the appropriate amine are obtained 2,9-diethyl-, di-n-propyl-, di-n-butyl-, di-n-octyl-, di-cyclopentyl-, and dicycloheptyl - 1,2,3,4,7,8,9,10 - octahydro - 2,9-diaza - 4,7 - dioxachrysene; (2) as in (1), using naphthalene-1,5-diol and the appropriate amine are obtained 2,8-dicyclohexyl-, and di-n-propyl - 1,2,3,4,7,8,9,10 - octahydro - 2,8 - diaza-4,10-dioxachrysene; (3) cyclohexylamine in methanol is treated with formalin and naphthalene-2,6-diol in methanol, the mixture refluxed and poured into water when 3,9-dicyclohexyl-1,2,3,4,7,8,9,10 - octahydro - 3,9 - diaza - 1,7-dioxachrysene crystallizes; similarly are obtained 3,9-dimethyl-, diethyl, di-n-propyl, diisopropyl, di - n - butyl and di - n - pentyl-1,2,3,4,7,8,9,10 - octahydro - 3,9 - diaza - 1,7-dioxachrysene.