The Synthesis of Some 6-Methoxy-8-(β-aminopropionylamino)-quinolines

Abstract

The 2,4-dinitrophenylhydrazone prepared in the usual manner from the product obtained by acid hydrolysis of 2-ethoxytetrahydropyrane melted at 109°and gave no depression in a mixed melting point determination with the 2,4-dinitrophenylhydrazone prepared from 5-hydroxy-pentanalU 2,4-Pentadienal (VII).-To a solution of 40 ml. of 85% phosphoric acid in 200 ml. of water was added with stirring 40 g. cf 2-ethoxy-A:,-dihydropyrane. Within a few minutes the solution became homogeneous. This solution was added drop wise to a solution of 50 ml. of 85% phosphoric acid in 200 ml. of water which was already undergo!):g steam (listillation.Steam distillation was continued until the distillate no longer had the characteristic' odor of pentadienal. The steam distillate was itself steam distilled to concentrate the aldehyde. After the addition of potassium chloride, the pentadienal was extracted with ether and dried over sodium sulfate. After removal of the ether under reduced pressure, the aldehyde was distilled; yield 14 g. (55%), , n2i d 1.5163.