Synthesis, Characterization, Crystallographic Studies of 5-Acetyl-8-hydroxyquinoline and Their Chalcone Derivatives

C.B. Vagish1,, Karthik Kumara2,, N.K. Lokanath2,, K. Ajay Kumar1, and P.G. Chandrasherkar1,*,

1Department of Chemistry, Yuvaraja′s College, Mysuru-570005, India

2Department of Studies in Physics, University of Mysore, Mysuru-570005, India

*Corresponding author: E-mail: pgc2031@gmail.com

Abstract

An efficient, easy and one pot synthesis for the Friedel-Craft acetylation reaction of quinolines was developed. The reaction between 8-hydroxyquinoline and acetyl/benzoyl chloride in nitrobenzene immediately flocculates as yellow precipitate. On further addition of Lewis acid causes the Friedel-Craft acetylation leads to formation of acetylated quionlines in good yields. The structure of compound 5-acetyl-8-hydroxyquinoline (3) was confirmed by single crystal X-ray diffraction studies. The compound crystallizes in the monoclinic crystal system with the space group P21/c. The synthesized acetylated quionlines undergoes condensation reaction with aromatic aldehydes leads to 8-hydroxyquinoline chalcones derivatives. The products were characterized by spectral studies, elemental analysis and single crystal X-ray diffraction studies.

Keywords

Friedel-Craft acetylation, 8-Hydroxyquinoline, Chalcones.

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