ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

The reduction of 1-benzyloxymethyl-3,4-dihydro-6,7-dimethoxyisoquinoline

I. Ježo, M. Karvaš, and K. Tihlárik

Slovak Academy of Sciences, Bratislava

Abstract: It was established that by the redn. of 1-benzyloxymethyl-3,4- dihydro-6,7-dimethoxyisoquinoline with Zn in HCl or with metal Na in abs. EtOH, D,L-Salsolidine (I) was formed in place of the expected 1-benzyloxymethyl-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline (II). I b. 125°/0.2 mm., the base m. 52-3°, the HCl salt m. 194° (EtOH); picrate m. 201° (EtOH), picrolonate m. 238-9° (EtOH) 0.5 H₂PtCl₆ salt m. 208° (EtOH). With Sn in HCl, the expected II was formed; HCl salt m. 212-13° (EtOH); picrate m. 211-12° (EtOH); methiodide m. 208-9° (EtOH); 0.5 H₂PtCl₆ salt m. 212-13° (EtOH); picrolonate m. 193-4° (EtOH). The action of Al amalgam in damp Et₂O did not result in the redn. of the double bond and the original II could be isolated from the reaction medium.

Full paper in Portable Document Format: 141a38.pdf (in Slovak)

Chemical Papers 14 (1) 38–43 (1960)