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Route to the tritiation of carbon atom‐9 of carcinogenic fluorenylhydroxamic acids
Author(s) -
Gutmann H. R.,
Bell P.
Publication year - 1974
Publication title -
journal of labelled compounds
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0022-2135
DOI - 10.1002/jlcr.2590100210
Subject(s) - chemistry , amine gas treating , fluorene , medicinal chemistry , triethylamine , hydrogenolysis , acetic acid , methylene , acetic anhydride , catalysis , carbon atom , nitro , alcohol , acetanilide , organic chemistry , ring (chemistry) , polymer , alkyl
The selective tritiation of the methylene carbon atom of the carcinogens, N‐fluoren‐3‐yl‐and N‐fluoren‐1‐ylacetohydroxamic acid, has been investigated. The synthesis of N‐[9‐ 3 H]fluoren‐3‐ylacetohhydroxamic acid involves hydrogenolysis of 3‐aminofluoren‐9‐one to [9‐ 3 ]fluoren‐3‐amine with LiAl 3 H 4 ‐A1C1‐. The tritiated amine is oxidized to 3‐nitro‐[9‐ 3 H]fluorene with m‐chloroperoxybenzoic and the labeled nitro compound is partially hydrogenated to the 3 H‐hydroxamic acid with 10% Pd–C catalyst in presence of acetic anhydride and triethylamine or dimethylaniline. N‐[9‐ 3 H]fluoren‐1‐ylacetohydroxamic acid may be obtained from 1‐aminofluoren‐9‐one by the same procedure. However, N‐[9‐ 3 H]fluoren‐2‐ylacetohydroxamic acid cannot be prepared in this way because reduction of 2‐aminofluoren‐9‐one with LiA1H4‐A1C1 3 does not proceed beyond the alcohol, 2‐aminofluoren‐9‐ol.