Nickel-Catalyzed Nitration of 8-Benzamidoquinoline

Jacob Smothers*, Andreas Baur, and Jessica M. Hoover
C. Eugene Bennett Department of Chemistry, West Virginia University, Morgantown, WV 26506

Presentation No.: 113

Assigned Category (Presentation Format): Physical Sciences (Poster Presentations)

Student’s Major: Chemistry, Biology

C-H functionalization is an important technique for synthesizing compounds that would otherwise be difficult to produce using traditional methods. Due to the presence of many C-H bonds available for activation, traditional methods, which involve the use of both nitric acid and sulfuric acid, lead to mixtures of products and can be ineffective for producing specific isomers of a desired compound in high yields. Catalytic systems allow for milder conditions and greater ability to produce one specific isomer in relatively high yield. In this study the nickel-catalyzed nitration of 8-benzamidoquinoline is used to examine the role of different nickel sources in the selective C-H activation of 8-aminoquinoline derivatives. A number of different nickel sources as catalysts were screened in acetonitrile in the presence of pivalic acid, tert-butyl nitrite, and N2 gas. From this study, it appears that a number of different nickel sources are able to serve as effective catalysts for the nitration of 8-aminoquinoline derivatives. Additionally, some nickel sources are more selective than others, and some produce higher yields of the desired product.

Funding: National Institutes of Health

Program/mechanism supporting research/creative efforts: WVU's SURE program (Rita Rio & Michelle Richards-Babb)