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Synthesis of selected 14C-labeled carcinogenic aromatic amines

✍ Scribed by Thomas P. Johnston; Anita T. Shortnacy; Ruby H. James

Publisher
John Wiley and Sons
Year
1978
Tongue
French
Weight
515 KB
Volume
15
Category
Article
ISSN
0022-2135

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✦ Synopsis

4,4'-(Methylene-'T)bis[ N, N-dimethylbenzenamine] (3, 2,4-'4C, 6-trimethylbenzenamine hydrochloride (3, and 4-chlor0-2-(methyl-~~C)benzenarnine hydrochloride (3 were synthesized for an investigation of the metabolism of carcinogenic compounds. Evaluations of synthetic routes led to the following preferred methods: the LiAlH,-AlCl, reduction of carbonyl-labeled Michler's ketone for 2 the Hofmann-Martius rearrangement of the salt formed from 2,6-dimethylbenzenamine and iodomethane-14C for 2, and the nitration of (methyl-W)benzene followed by reduction with stannous chloride in hydrochloric acid for 3. The free baees o f 2 and parative thin-layer chromatography, but the free base of 1 was not completely separated from a tetramethylbenzenamine.

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