Preparation of tritium-labeled compounds. VI. Nafoxidine hydrochloride by clemmensen reduction and by solvent exchange of intermediates

✍ Scribed by Richard C. Thomas; Daniel Lednicer

• Publisher: John Wiley and Sons
• Year: 1978
• Tongue: French
• Weight: 268 KB
• Volume: 14
• Category: Article
• ISSN: 0022-2135
• DOI: 10.1002/jlcr.2580140209

✦ Synopsis

Abstract

Tritium‐labeled nafoxidine hydrochloride, 1‐{p‐[2‐(N‐pyrro‐lidino) ethoxy]phenyl}‐3,4‐dihydro‐6‐methoxy‐2‐phenylnaphthalene hydrochloride (I), having two different intramolecular distributions of tritium, was prepared from 6‐methoxy‐2‐phenyl‐1‐tetralone (IV). I was labeled in the 4 position by incorporation of IV which had been labeled in the 4 position by Clemmensen reduction of 2‐phenyl‐4‐(m‐methoxyphenyl)‐4‐ketobutyric acid (II) in the presence of tritiated water, followed by cyclization of the resulting 2‐phenyl‐4‐(m‐methoxyphenyl) butyric acid (III). I was labeled in the aromatic positions of its phenylnapthalene moiety at a higher specific activity by incorporation of IV which had been generally labeled by exchange with tritiated trifluoroacetic acid.