Improvements in or relating to alkoxybenzylisoquinolines and salts thereof

摘要

The invention comprises alkoxybenzyl-isoquinolines of the formula FORM:0674800/IV (b)/1 where R1 and R2 are different alkoxy radicals of 1-3 carbon atoms, one being methoxy, and their addition salts; they are prepared by ringclosure of the appropriate a -methyl-homoveratryl-alkoxyphenylacetamides with phosphorus oxychloride and dehydrogenation of the resulting 3 : 4-dihydro-isoquinolines, e.g. with palladium. The products form salts with mineral and organic acids, e.g. with hydrochloric, hydrobromic, hydriodic, sulphuric, nitric, phosphoric and citric acids. Examples show the production of the 31-ethoxy-41-methoxy, 41-ethoxy-31-methoxy and 31-methoxy-41-isopropoxy compounds and their salts. a -Methylhomoveratrylamine is made by (1) addition of hydrogen bromide to eugenol methyl ether, followed by treatment with ammonia, or (2) catalytic hydrogenation of 1 - (31 : 41 - dimethoxyphenyl) - 2 - propanone oxime, prepared from the ketone in the usual way. a - Methylhomoveratryl - alkoxyphenylacetamides are made by reacting the above amine with the appropriate alkoxyphenylacetic acids, e.g. the 3-ethoxy-4-methoxy, 4-ethoxy-3-methoxy and 3-methoxy-4-isopropoxy-acids.