Nickel-Catalyzed Nitration of 8-Benzamidoquinoline

Jacob B. Smothers*, Andreas Baur, and Jessic M. Hoover

C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506

Presentation Category: Physical Sciences & Engineering (Poster Presentation #153)

Student’s Major: Chemistry

C-H functionalization is an important technique for making compounds that would otherwise be difficult to make using other methods. In the case of 8-benzamidoquinoline, there are a number of C-H bonds that can be functionalized by addition of a nitro substituent. This means that there would be multiple different positions that could potentially be nitrated using traditional methods of nitration. In addition, traditional methods tend to rely on reactions conditions that are relatively harsh: a mixture of both nitric acid and sulfuric acid. Both of these are strong acids that have little to no selectivity, and therefore, it is necessary to develop catalysts for selective functionalization reactions for compounds like 8-benzamidoquinoline that also do not involve conditions that are particularly harsh. The focus of this research project is to explore nickel compounds as catalysts for the selective C-H nitration of the C5 position of an 8-aminoquinoline derivative. 8-aminoquinoline is an important starting point in the synthesis of many natural products, pharmaceuticals, and pesticides and selective functionalization of 8-aminoquinoline derivatives will hopefully lead to the development of new methods for synthesizing biologically and industrially important compounds. This poster will describe the synthesis of the 8-benzamidoquinoline starting material and the catalytic nitration reactions. Preliminary data suggest that nickel is important for both the efficiency and regioselectivity of the nitration reaction.

Funding: National Institutes of Health

Program/mechanism supporting research/creative efforts: WVU's Research Apprenticeship Program (RAP) & accompanying HONR 297-level course