Synthesis and Characterization of Alkyl and Aryl‐(4‐methyl‐6‐nitro‐quinolin‐2‐yl)amines: X‐Ray Structures of Ethyl and Cyclohexyl‐(4‐methyl‐6‐nitro‐quinolin‐2‐yl)amine

Abstract

We have synthesized and characterized a series of alkyl and aryl‐(4‐methyl‐6‐nitro‐quinolin‐2‐yl)amines through a high‐yield, three‐step procedure starting from 4‐methylquinolin‐2‐ol. Nitration using concentrated nitric/sulfuric acids, followed by chlorination in phosphorus oxychloride, yielded 2‐chloro‐4‐methyl‐6‐nitro‐quinoline. All of the intermediates and aminated products have been characterized by multinuclear (¹H and ¹³C) NMR spectroscopy, elemental analysis, and, in the case of the two title compounds (ethyl and cyclohexyl‐(4‐methyl‐6‐nitro‐quinolin‐2‐yl)amine), a single crystal X‐ray structure was obtained to verify the nature of the new materials.

Keywords:

• Quinolinamines
• substituted amines
• X‐ray structure

Acknowledgments

M. D. R acknowledges support from NASA and the Louisiana Board of Regents through the LaSpace Program (NASA Grant NGT5‐40115 and BOR Contract NASA/LEQSF 2001‐2005‐LaSpace). We are grateful to Scott McKinley (Iowa State University) for assistance in obtaining the NMR spectra and to Wayne Hyde for his helpful discussions. We thank Margaret Cochran (Louisiana Scholars' College) and Austin Temple (NSU) for their constant support of this undergraduate research through the NASA‐JOVE program and we thank UW—Fox Valley for travel assistance.