1966 年 86 巻 10 号 p. 979-983
After benzylation of methyl 3.5-dihydroxy-4-methoxybenzoate (III), the product was submitted to the McFadyen-Stevens reaction and derived to the amine (IX) in several steps. Condensation of IX with 4-methoxyphenacetyl chloride by the Schotten -Baumann reaction gave the amide (X) which was cyclized to XI by the usual Bischler-Napieralski reaction and debenzylated to the obtain objective 3, 4-dihydro-7-methoxy-1-(4-methoxybenzyl)-6, 8-isoquinolinediol (II). Application of 1 mole of diazomethane to 1 mole of II resulted in the formation of a phenolic base (XIII) in which the hydroxyl in 8-position had been methylated, besides the compound (XII) with all the hydroxyl groups in II methylated. XIII was proved by deriving it to XIV. However, the objective 8-hydroxy derivative with the 6-hydroxy methylated was not obtained so that it was impossible to derive the product to the objective I through its methiodide.