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Two syntheses of 7,8‐dichloro‐1,2,3,4‐tetrahydroisoquinoline‐1‐ 14 C
Author(s) -
Mendelson Wilford L.,
Villani Anthony J.,
Petka Louis A.,
Spainhour Charles B.
Publication year - 1984
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580211010
Subject(s) - chemistry , isoquinoline , yield (engineering) , ammonium chloride , amine gas treating , tetrahydroisoquinoline , chloride , alcohol , tritium , base (topology) , sequence (biology) , medicinal chemistry , organic chemistry , materials science , metallurgy , mathematical analysis , biochemistry , physics , mathematics , nuclear physics
Two complementary radiosynthetic routes to the potent PNMT inhibitor 7,8‐dichloro‐1,2,3,4‐tetrahydroisoquinoline‐1‐ 14 C( 1 ) from 2,3‐dichlorobenzaldehyde‐ formyl ‐ 14 C( 4 ) are described. In the Pomeranz‐Fritsch sequence isoquinoline 6 was prepared from Schiff's base 5 . Catalytic hydrogenation of 6 (H 2 /PtO 2 ) furnished 1 in 28% radiochemical yield from 4 . In the aluminum chloride fusion sequence, 4 was converted via amino alcohol 7 to chloro amine 8 . Treatment of the latter with aluminum chloride/ammonium chloride (fusion, 190°C) yielded labeled 1 in 31% radiochemical yield from 4 .
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