A Simple Preparative Synthesis of Isomeric 2-Chloroquinolinecarboxylic Esters

Yurii V. Ishkov; Vira V. Veduta; Nadiia F. Fedko; Natalia M. Bohdan

doi:10.24959/ophcj.23.298574

Authors

Yurii V. Ishkov I.I. Mechnikov Odesa National University, Ukraine https://orcid.org/0000-0003-1228-3880
Vira V. Veduta I.I. Mechnikov Odesa National University, Ukraine https://orcid.org/0000-0002-1151-650X
Nadiia F. Fedko I.I. Mechnikov Odesa National University, Ukraine https://orcid.org/0000-0003-1222-9817
Natalia M. Bohdan Institute of Organic Chemistry of the National Academy of Sciences of Ukraine, Ukraine https://orcid.org/0000-0002-6522-1694

DOI:

https://doi.org/10.24959/ophcj.23.298574

Keywords:

2-chloroquinoline, esters, oxidation, quinolone-2, chlorination

Abstract

A simple two-stage method for the synthesis of isomeric esters of 2-chloroquinoline-5-, 6-, 7-carboxylic acids by successive oxidation and chlorination reactions of methyl quinoline-5-, 6-, 7-carboxylates has been developed. The target compounds have been obtained in acceptable yields using readily available reagents, simple transformations, and purification methods. Quinoline-8-carboxylic acid ester is unreactive under these conditions. The ester of 2-chloroquinoline-8-carboxylic acid has been obtained with an overall yield of 55%, starting from 8-methylquinoline. The multi-stage process is paid off by the fact that several transformations occur in one reaction cycle. All the methods developed can be used for the synthesis of target compounds on a multigram scale. Intermediate 2(1H)-oxoquinoline carboxylates are promising compounds in the synthesis of functionalized and condensed heterocycles.

Supporting Agency

The authors received no specific funding for this work.

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