Quinamine

Description

One of the minor Cinchona alkaloids, this base was first isolated by Hesse from the bark of C. succirubra and subsequently in the barks of several of this species, especially in that of C. ledgeriana. It yields a series of crystalline salts, e.g. the hydrochloride monohydrate, m.p. 166-7°C; [α]_D + 102.8° (H20); the hydriodide, m.p. 224°C; [α]_D + 84.8° (EtOH); nitrate, m.p. 186-8°C; [α]_D + 95° (H20) and the picrate which forms small yellow needles from boiling H20, m.p. 175-6°C; [α]_D + 90° (Me2CO). The nitroso derivative is amorphous but yields a crystalline picrate, m.p. 161 ° C and an acetyl derivative, m.p. 137- 141°C. The alkaloid also forms a methiodide, m.p. 250-1 0 C; [α]_D + 114.2° and a methochloride, m.p. 237-240°C; [α]_D + 111.9°. Catalytic hydrogenation furnishes the dihydro derivative, m.p. 184-5°C; [α]_D + 119.8°, yielding a picrate, m.p. 176-8°C and a methiodide, m.p. 219-225°C. In contrast to the other Cinchona alkaloids, this base does not yield a quinoline derivative on oxidation but gives, instead, a viny1quinuclidinecarboxy1ic acid, m.p. 206-8°C; [α]_D + 57.9° (CHCI 3 ) which may be isolated as the characteristic sop per salt.

References

Hesse., Ber., 5, 265 (1872)
Henry, Kirby, Shaw., J. Chem. Soc., 524, 528 (1945)
Henry, Kirby, Shaw., ibid, 735 (1949)
Goutareletal., Helv. Chim. Acta, 33, 150, 164 (1950)
Benz et al.: J. Chem. Soc., 1130, 1485 (1950)