ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
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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)

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