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Synthesis of carbon C‐14 labelled 2‐phenyl‐4‐alpha‐alkylaminomethyl‐quinolinemethanol: A potential anti‐leishmaniasis agent
Author(s) -
Wang Theodore S. T.,
Fawwaz Rashid A.,
Van Heertum Ronald L.
Publication year - 1995
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.2580360709
Subject(s) - chemistry , yield (engineering) , medicinal chemistry , quinoline , benzene , alkylation , claisen condensation , grignard reaction , ethylene oxide , acylation , chloride , carbon 14 , oxide , nuclear chemistry , ethylene , organic chemistry , catalysis , materials science , polymer , physics , copolymer , quantum mechanics , metallurgy , reagent
Using sodium acetate, [1‐ 14 C] as a starting material, a total of seven steps were required to synthesize the title compound. This involved acylation of ortho‐dichlorobenzene to form dichloroacetophenone, [2‐ 14 C] (I). The 2‐phenyl‐4‐quinoline carboxylic acid, [2‐ 14 C] (II) was prepared by the Pfitzinger reaction from (I) and dichloroisatin. Compound II was converted to the acid chloride (III) by reaction with SOCl 2 in benzene. Grignard condensation reaction of (III) yielded 4‐quinolylmethylketone, [2‐ 14 C] (IV) which was then converted to the bromomethylketone (V). Compound V was reacted with NaBH 4 to form the ethylene oxide (VI). Alkylation of the oxide yielded the title compound (VII). The overall radiochemical yield was 10.1% and the specific activity was 3.0 mCi/mmol, with a radiochemical purity of > 99.5%.