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Synthesis of carbon C-14 labelled 2-phenyl-4-alpha-alkylaminomethyl-quinolinemethanol: A potential anti-leishmaniasis agent

✍ Scribed by Theodore S. T. Wang; Rashid A. Fawwaz; Ronald L. Van Heertum

Publisher
John Wiley and Sons
Year
1995
Tongue
French
Weight
297 KB
Volume
36
Category
Article
ISSN
0022-2135

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✦ Synopsis

Abstract

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%.

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