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Synthesis of selected 14 C‐labeled carcinogenic aromatic amines
Author(s) -
Johnston Thomas P.,
Shortnacy Anita T.,
James Ruby H.
Publication year - 1978
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.2580150172
Subject(s) - chemistry , hydrochloride , hydrochloric acid , nitration , chloride , free base , benzene , methylene , ketone , organic chemistry , carcinogen , salt (chemistry) , medicinal chemistry
4 , 4 ′‐(Methylene‐ 14 C)bis[N, N‐dimethylbenzenamine] ( 2 ), 2, 4‐ 14 C, 6‐trimethylbenzenamine hydrochloride ( 7 ), and 4‐chloro‐ 2 ‐(methyl‐ 14 C)benzenamine hydrochloride ( 18 ) were synthesized for an investigation of the metabolism of carcinogenic compounds. Evaluations of synthetic routes led to the following preferred methods: the LiAlH 4 ‐AlCl 3 reduction of carbonyl‐labeled Michler's ketone for 2 , the Hofmann‐Martius rearrangement of the salt formed from 2 , 6 ‐dimethyl‐benzenamine and iodomethane‐ 14 C for 7 , and the nitration of (methyl‐ 14 C)benzene followed by reduction with stannous chloride in hydrochloric acid for 18 . The free bases of 7 and 18 were isolated from complex product mixtures by preparative thin‐layer chromatography, but the free base of 7 was not completely separated from a tetramethylbenzenamine.