WWRC 83-10
Synthesis and High Performance Liquid
Chromatography of w-(3-Substituted-2-OXO-1-Pyridyl)-Alklylsulfonates for Use
as Water Tracing Compounds
Introduction
The purpose of this research was to study the synthesis and applications of
two new homologous series of 1,3-distributed 2-pyridones as possible
site-specific water tracing compounds. The compounds were designed to increase
the solubility of the parent molecules as well as to create separately
identifiable compounds for analysis with high performance liquid chromatography
(HPLC). The synthesis of the two specific starting parent molecules of
interest, 1-H-2-oxo-3-phenylpyridine (1) and 1-H-2-oxo-3-carbamoylpyridine (4)
are shown in Figure 1. Compound 1 was synthesized by a procedure designed by
Bush, following work of Boekelheide, which involves
rearrangement of a pyridine N-oxide. Compound 4 was synthesized from 2-chloronicotinic
acid.
The course of this research required a large amount of 2-hydroxynicotinic
acid. Since an efficient large-scale synthetic method had not been reported for
forming the precursor 2-chloronicotinic acid, we designed such a method based on
a literature patent.
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