Novel and Efficient Procedure for the Preparation of Two Pyridine Dicarboxylic Acid Derivatives

G U Guoliang,L U Ming

doi:10.1155/2011/120730

Abstract

New strategies for the synthesis of two pyridine dicarboxylic acid derivatives namely; 4-(2-(2,6-dicarboxypyridin-4-yl)vinyl)pyridine-2,6-dicarboxylic acid and 2,6-bis(2-(2,6–dicarboxy-pyridin-4-yl)vinyl)pyridine have been described. New oxidant used is a good example of green chemistry technology and the synthesis procedure harvest a high-purity product at a high yield.

Highlights

Our research group has recently been interested in synthesis of the pyridine dicarboxylic acid derivatives with rigid conjugated planar structure, which would be beneficial to the electronic negotiability[1], as many of them are useful in the field of fiber-optic telecommunications systems2~5 and time resolved fluoroimmunoassay (TR-FIA)6~7
We report here the new synthesis routes, in which the oxidants sodium salt of 2-nitrpropane and recycled K3Fe(CN)[6] were used
The reaction mixture was cooled to the room temperature and filtered to obtain the colorless solid 4

Summary

Introduction

Our research group has recently been interested in synthesis of the pyridine dicarboxylic acid derivatives with rigid conjugated planar structure, which would be beneficial to the electronic negotiability[1], as many of them are useful in the field of fiber-optic telecommunications systems2~5 and time resolved fluoroimmunoassay (TR-FIA)6~7.In recent years, increasing attention has been focused on organic reactions in which environmental pollution reduced and aqueous media used. To a solution of compound 1 (3.0 g, 13.3 mmol) in anhydrous CHCl3 (25 mL), sulfuryl dichloride (2.4 g, 20.0 mmol) as added drop wise under nitrogen atmosphere at -5o C with continuous stirring for 40 min. Excess solvent was removed under reduced pressure and the crude product was purified by recrystallization from ethanol to give the flaxen solid 2 (yield 2.8 g) after drying in vacuum. The compound 2 (37.30 g, 0.15 mol) was added to the mixture solution and heated to reflux for 4 h.

Results

Conclusion