Abstract
Conditions for the preparation of N-phenyl-5-acenaphthenylamines by decarboxylation of N-(5-acenaphthenyl) anthranilic acids (I) were examined and 7-alkyl (or aryl)-4, 5-dihydroindeno[1, 7-bc]acridine derivatives (IV) were prepared from (II) by the Bernthsen method. In this reaction, the amount of fused zinc chloride added was found to give a great effect on the yield of (IV). In the case of (IV:X=Cl, R=CH3), two isomers were isolated and their structures were determined. Condensation of active methyl in 7-position of (IV:R=CH3) and p-nitrosodimethylamine was examined and an interesting fact was observed. It was found that the presence of an alkaline catalyst (sodium carbonate, potassium carbonate, or piperidine) caused extremely poor yield, while in the presence of a mineral acid, especially hydrochloric acid, a good yield was obtained. In this case, the chief product was found to be the nitrone compound (X) and only a small amount of the anil (IX) was formed. These (IX) and (X) easily formed the 7-formyl compound (XI) by treatment with dil. hydrochloric acid. Condensation of (XI) with various amines gave Schiff bases (XII), and the acrylic acid (XIII) was prepared by the condensation of (XI) and malonic acid by the Perkin reaction. The methyl group in 7-position was found to decrease in activity in this reaction by the presence of chlorine in 10-position.
