Abstract
In the preceding paper, it was shown that the product obtained by cleavage reaction of O-methyldomesticine (I) with metallic sodium in liquid ammonia was solely a phenolic base (hydrochloride, m. p. 256°(decomp.), C18H19O2N⋅HCl) and its structure and that of its O-methylated compound (hydrochloride, m. p. 233°(decomp.), C19H21O2N⋅HCl, [α]D20+86°(90% EtOH)) were found by decomposition reactions to correspond to (II) and (III).
In the present series of work, dl-2, 10-dimethoxyaporphine (III) was synthesized by the route shown in Chart 1 and comparison of (III) with the O-methylated cleaved base showed that the two are identical. It follows, therefore, that, since it is known that a methylenedioxy group undergoes one-sided cleavage reaction by metallic sodium in liquid ammonia to newly produce one phenolic hydroxyl, the phenolic base formed by the cleavage reaction of O-methyldomesticine (I) is known to be 2-methoxy-10-hydroxyaporphine (II). This has revealed that the methoxyl group in 1-position of the aporphine ring in (I) is completely liberated by the reaction with sodium in liquid ammonia and this is a new example rarely seen in this kind of reaction.
