8063. Quininone
Nomenclature
CAS number: 84-31-1
(8α)-6′-Methoxycinchonan-9-one. C20H22N2O2; mol wt 322.40.
C 74.51%, H 6.88%, N 8.69%, O 9.93%.
Description and references
By careful oxidation of quinine or quinidine: Rabe, Kuliga, Ann. 364, 346, 349 (1909); Woodward et al., J. Am. Chem. Soc. 67, 1425 (1945). Alternate procedure: Rabe, Kindler, Ber. 51, 466 (1918). Prepn of amorphous epimeric mixture of quininone and quinidinone from quinotoxine: Gutzwiller, Uskokovic, Helv. Chim. Acta 56, 1494 (1973).
Properties
Crystals from ether, mp 108° (rapid heating). Shows mutarotation, final [α]D20 +76° (c = 2 in alcohol). Alkaline reaction to litmus. Freely sol in alcohol, ether, chloroform, benzene. Almost insol in water and petr ether.Derivative
Hydrochloride.C20H22N2O2.HCl; mol wt 358.86.
C 66.94%, H 6.46%, N 7.81%, O 8.92%, Cl 9.88%.