Studies on Nitrogen-containing Heterocyclic Compounds. XXXVIII. 2 Step Syntheses of Cyclopropa [c] quinoline Derivatives from Quinoline Derivatives, via the von Braun Reaction

1-Cyano-2-methoxy-1, 2-dihydroquinolines (I) were dissolved in chloroform or bromo-form, 50% sodium hydroxide solution was added in the presence of a small quantity of interphase transition catalyst, and the mixture was stirred at room temperature, by which the corresponding 3-cyano-1, 1-dichloro (or dibromo)-2-methoxy-1a, 2, 3, 7b-tetrahydro-1H-cyclopropa [c] quinoline derivatives (II) were obtained. I can be obtained easily in one step from the commercial quinoline derivative so that this reaction is a useful two-step synthesis of cyclopropa [c] quinoline derivatives (II) from commercial quinoline derivatives.