H. Gutmann, P. Bell
Apr 1, 1974
Citations
0
Influential Citations
3
Citations
Journal
Journal of Labelled Compounds and Radiopharmaceuticals
Abstract
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-[9-3H]fluoren-3-ylacetohhydroxamic acid involves hydrogenolysis of 3-aminofluoren-9-one to [9-3]fluoren-3-amine with LiAl3H4-A1C1-. The tritiated amine is oxidized to 3-nitro-[9-3H]fluorene with m-chloroperoxybenzoic and the labeled nitro compound is partially hydrogenated to the 3H-hydroxamic acid with 10% Pd–C catalyst in presence of acetic anhydride and triethylamine or dimethylaniline. N-[9-3H]fluoren-1-ylacetohydroxamic acid may be obtained from 1-aminofluoren-9-one by the same procedure. However, N-[9-3H]fluoren-2-ylacetohydroxamic acid cannot be prepared in this way because reduction of 2-aminofluoren-9-one with LiA1H4-A1C13 does not proceed beyond the alcohol, 2-aminofluoren-9-ol.