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WWRC 83-10
Synthesis and High Performance Liquid Chromatography of w-(3-Substituted-2-OXO-1-Pyridyl)-Alklylsulfonates for Use as Water Tracing Compounds


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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