8-Aminoquinoline is the 8-amino derivative ofquinoline. Often abbreviated AQ, it is a pale yellow solid. It is structurally analogous to8-hydroxyquinoline.[2]
The derivativesprimaquine,tafenoquine andpamaquine have been tested for anti-malaria activity.[3][4] Primaquine is still used routinely worldwide as part of the treatment ofPlasmodium vivax andPlasmodium ovale malaria, although how it prevents malarial recurrences is not, at present, clear.[5] Tafenoquine was approved for medical use in Australia and in the United States in 2018.[6][7]
The original synthesis of AQ involved nitration of quinoline to give a mixture of the 5- and 8-nitroderivatives, which were separated by distillation and sublimation. Reduction of the 8-nitro isomer with tin powder in the presence of hydrochloric acid gave the amines.[10] AQ can also be produced by amination of 8-chloroquinoline.
^Van Meervelt L, Goethals M, Leroux N, Zeegers-Huyskens T (1997). "X-ray and vibrational studies of 8-aminoquinoline. Evidence for a three-center hydrogen bond".Journal of Physical Organic Chemistry.10 (9):680–686.doi:10.1002/(SICI)1099-1395(199709)10:9<680::AID-POC902>3.0.CO;2-Y.
^Rej S, Ano Y, Chatani N (2020). "Bidentate Directing Groups: An Efficient Tool in C–H Bond Functionalization Chemistry for the Expedient Construction of C–C Bonds".Chemical Reviews.120 (3):1788–1887.doi:10.1021/acs.chemrev.9b00495.PMID31904219.S2CID209895281.
^Corbet M, De Campo F (2013). "8-Aminoquinoline: A Powerful Directing Group in Metal-Catalyzed Direct Functionalization of C-H Bonds".Angewandte Chemie International Edition.52 (38):9896–9898.doi:10.1002/anie.201303556.PMID23939922.
