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Synthesis of isotopically labeled tri‐ p ‐tolylamine
Author(s) -
Kesling Brian D.,
Söderberg Björn C.,
Gullion Terry
Publication year - 2000
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 - 10.1002/1099-1344(200009)43:10<1059::aid-jlcr392>3.0.co;2-d
Subject(s) - chemistry , nitration , amination , halogenation , palladium , catalysis , organic chemistry , medicinal chemistry , combinatorial chemistry
Three isotopically labeled tri‐ p ‐tolylamines, 15 N, 15 N 2 D 27 , and mono‐ 13 CH 3 have been prepared using zeolite mediated bromination or nitration of toluenes as one of the key steps. The obtained‐4‐nitrotoluenes were reduced to 4‐aminotoluenes, and coupled, via a palladium catalyzed amination reaction, with 4‐bromotoluenes to afford di‐ and tri‐ p ‐tolylamines. The di‐ p ‐tolylamines were readily transformed into tri‐ p ‐tolylamines using the same palladium catalyzed methodology. Copyright © 2000 John Wiley & Sons, Ltd.