Quininone
Title: Quininone
CAS Registry Number: 84-31-1
CAS Name: (8a)-6¢-Methoxycinchonan-9-one
Molecular Formula: C20H22N2O2
Molecular Weight: 322.40
Percent Composition: C 74.51%, H 6.88%, N 8.69%, O 9.93%
Literature 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 [a]D20 +76° (c = 2 in alcohol). Alkaline reaction to litmus. Freely sol in alcohol, ether, chloroform, benzene. Almost insol in water and petr ether.
Melting point: mp 108° (rapid heating)
Optical Rotation: [a]D20 +76° (c = 2 in alcohol)
 
Derivative Type: Hydrochloride
Molecular Formula: C20H22N2O2.HCl
Molecular Weight: 358.86
Percent Composition: C 66.94%, H 6.46%, N 7.81%, O 8.92%, Cl 9.88%
Properties: Hygroscopic crystals, mp 212°. Final [a]D18 +59° (c = 2 in abs alcohol).
Melting point: mp 212°
Optical Rotation: [a]D18 +59° (c = 2 in abs alcohol)

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