Abstract
Mannich reaction of 1-chloro-4-isoquinolinol (1) with dimethylamine and formalin afforded the base, 1-chloro-3-dimethylaminomethyl-4-isoquinolinol (2), and a by-product, 1, 1'-dichloro-3, 3'-methylenedi-4-isoquinolinol (3). The reaction of 1 with formalin in H2SO4 gave 6-chloro-1, 3-dioxino [5, 6-c] isoquinoline (4). The reactions of 1 with formalin and primary amines, and of 1 with acetaldehyde ammonia afforded the corresponding products, 1, 3-oxazino [5, 6-c] isoquinolines (5-7), in fair yields. Methyl 4-hydroxy-1-oxo-1, 2-dihydroisoquinoline-3-carboxylate (8) was converted into the carboxamide (9), which, on heating with a mixture of POCl3 and PCl5, afforded two chloro-cyano compounds 10 and 11 in a ratio of ca. 1 : 2. The reaction of 11 with hydrazine hydrate gave the 1-hydrazino compound (13).
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