H. Junhua
2011
Citations
0
Influential Citations
1
Citations
Journal
CIESC Journal
Abstract
2-Aminonicotinic acid is an important synthetic intermediate of many drugs.A novel four-step synthesis method for preparing 2-aminonicotinic acid from quinoline is developed.The overall yield of 2-aminonicotinic acid is up to 29% based on quinoline.The oxidation of quinoline gives 2,3-pyridine dicarboxylic acid,and after intramolecular dehydration mediated by acetic anhydride,2,3-pyridine dicarboxylic anhydride is obtained.Then,this anhydride is subjected to ammonolysis followed by Hofmann degradation reaction to introduce C(2)amino group,completing the synthesis of target molecule 2-aminonicotinic acid.NaClO3-H2SO4-CuSO4 is prominently superior to KMnO4 as oxidant to quinoline,so that the yield is improved to 65.2%.The conditions of anhydride ammonolysis and Hofmann degradation were also optimized.The developed synthetic technologies are suitable for large-scale preparation,and the highlights include low cost and availability of starting material,safe operation,simple separation and purification,and high purity of final product.The target product with 98% HPLC purity is characterized by 1H NMR and IR.