Answer to Question #109550 in General Chemistry for Daniel

Question

steps to the active component of chloroquine using column chromatography

Answer 1

Chloroquine is a 4-aminoquinoline compound that has been used extensively for the treatment and prevention of malaria.

Chloroquine Phosphate is the active component of chloroquine tablet.

The desired products were 

purified by column chromatography and characterized by 1H NMR and 13C NMR 

spectroscopy as well as HR-MS and elemental analysis.

Chloroquine phosphate is prepared as previously reported 180 with slight modifications.Chloroquine phosphate was doubly 

deprotonated at the 1- and 1’-positions by the action of n-butyllithium, previously activated 

by a solution of N,N,N’,N’-tetramethylethylenediamine (TMEDA) in hexanes. The phosphate is then reacted with Eschenmoser’s salt or (N,N’-

dimethyl)methyleneammonium iodide in THF to afford the crude product containing chloroquine phosphate(1).

Starting material (1) was purified by column chromatography on neutral alumina. The structure and purity of 1 was verified by 1H NMR spectroscopy and LR-MS.