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Synthesis of tritium labeled mazindol
Author(s) -
Dugger Harry A.,
Tabot Kenrick C.
Publication year - 1976
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.2580120312
Subject(s) - chemistry , mazindol , chlorobenzene , tritium , yield (engineering) , benzoic acid , dimethyl phthalate , organic chemistry , phthalic anhydride , hydrolysis , phthalic acid , nuclear chemistry , radiochemistry , catalysis , medicinal chemistry , phthalate , neuroscience , nuclear physics , dopamine , metallurgy , biology , physics , materials science
Mazindol was labeled with tritium in the 6,9 positions in low yield starting with dimethyl phthalate‐3,6‐ 3 H which was prepared by reduction of dimethyl 3‐chlorophthalate with tritium gas using 10% palladium on charcoal as a catalyst. The labeled dimethyl phathalate was hydrolisized with extensive loss of the label by exchange and after conversion to phthalic anhydride was condensed with chlorobenzene to give 2‐(p‐chlorobenzoyl) benzoic acid‐3,6‐ 3 H. This acid was converted in two steps into 5‐hyddroxy‐54‐imidazo [2,1‐a] isoindol‐6,9‐ 3 H (mazindol‐6,9‐ 3 H). In a similar fashion, mazindol‐7,8‐ 3 H was prepared in higher yields beginning with dimethyl 4‐chlorophthalate. There was no loss of the label during the hydrolysis of dimethyl Phthalate‐4,5‐ 3 H.