Hydrochloric Acid → Hydrochloric Acid

Participants

Reaction Steps

2.2 g. (±)-5,6,6a,7-Tetrahydro-1-hydroxy-2,9,10-trimethoxy-5-methyl-4H-dibenz(de,g)isoquinoline trifluoro acetate (see Example 3) are dissolved in 10 ml. of a mixture of toluene and dimethylformamide (9:1 v/v) and methylated with phenyltrimethylammonium hydroxide in a manner analogous to that described in Example 7. When the reaction is finished, the reaction mixture is evaporated in a vacuum and the residue is partitioned between water and methylene chloride. The organic phase is worked up in the usual manner and the crude product obtained is converted, either directly or after previous chromatography on silica gel with chloroform as eluent, into the hydrochloride by treatment with ethanolic hydrochloric acid. Crystallisation from ethanol/diethyl ether gives (±)-5,6,6a,7-tetrahydro-1,2,9,10-tetramethoxy-5-methyl-4H-dibenz(de,g)isoquinoline in the form of a yellow hydrochloride; m.p. 212°-225° C.

Provenance & Evidence