69-44-3

Usage

Chemical Properties

Yellow crystalline solid; odorless; bitter. Soluble in water; sparingly soluble in alcohol; very slightly soluble in benzene, chloroform, and ether.

Originator

Camoquin HCl,Parke Davis,US,1950

Uses

Medicine (antimalarial).

Manufacturing Process

72.8 g (0.5 mol) of p-aminophenol hydrochloride is dissolved in 500 cc of water and added to 99 g (0.5 mol) of 4,7-dichloroquinoline. After a few minutes of warming in a steam bath, 4-(4'-hydroxyanilino)-7-chloroquinoline hydrochloride, of sufficient purity for use in further experiments, precipitates as a yellow crystalline solid. Recrystallized from methanol, the MP is over 300°C. A mixture consisting of 13.5 g of 4-(4'-hydroxyanilino)-7-chloroquinoline hydrochloride dissolved in absolute ethanol is treated with a solution of 4.38 g of diethylamine and 1.8 g of paraformaldehyde in 20 cc of absolute ethanol. The reaction mixture is heated under reflux for 16 hours, evaporated to onehalf volume and the warm solution treated with an excess of hydrogen chloride dissolved in absolute ethanol. Acetone is added to the warm solution until it becomes turbid and then the solution is cooled. The crude dihydrochloride which separates is collected and purified by recrystallization from methanol; MP 240-242°C. By using an equivalent amount of 4-(4'-hydroxyanilino)-7-bromoquinoline in the above procedure, 4-(3'-diethylaminomethyl-4'-hydroxyanilino)-7- bromoquinoline dihydrochloride is obtained; MP (base) 206-208°C dec.

Brand name

Camoquin (Parke-Davis).

Therapeutic Function

Antimalarial

InChI:InChI=1/C20H22ClN3O.2ClH/c1-3-24(4-2)13-14-11-16(6-8-20(14)25)23-18-9-10-22-19-12-15(21)5-7-17(18)19;;/h5-12,25H,3-4,13H2,1-2H3,(H,22,23);2*1H

Upstream product

• 86-98-6 4,7-dichloroquinoline 
• 51387-92-9 4-amino-2-((diethylamino)methyl)phenol 
• 103-90-2 4-acetaminophenol 

Downstream Products

• 1021496-19-4 4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol tetrachlorocobaltate(II) salt 
• 107632-46-2 VO⁽²⁺⁾*(C₂H₅)2NCH₂C₆H₃OHNHC₉H₅NCl*SO₄^(2-)=VO(C₂H₅)2NCH₂C₆H₃OHNHC₉H₅NClSO₄ 

Relevant academic research and scientific papers

Continuous preparing method for amodiaquine hydrochloride

The invention provides a continuous preparing method for amodiaquine hydrochloride. The method is a continuous three-step reaction preparing method and has the advantages that an intermediate product prepared in the reaction step is not separated, and amodiaquine hydrochloride is directly prepared. The method is simple in technology, less equipment is occupied, operation is simple, water serves as reaction solvent, pollution of a system is small, and the method is suitable for industrial production.

Lewis acid-catalyzed generation of C-C and C-N bonds on π-deficient heterocyclic substrates

Focused microwave irradiation of a series of halogenated nitrogen heterocycles and different kinds of nucleophiles in the presence of a catalytic amount of indium trichloride leads to the efficient and completely regioselective generation of aromatic C-C and C-N bonds. The method is simple, rapid, general and inexpensive, and can be performed without the use of dried solvents. Most of the synthetized compounds are new and in many cases the work-up required only filtration. Furthermore, this is the first example of the use of a Lewis acid as a catalyst for heteroarylation, vinylation and amination reactions on π-deficient heterocyclic substrates.