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
Check Digit Verification of cas no
The CAS Registry Mumber 69-44-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 6 and 9 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 69-44:
(4*6)+(3*9)+(2*4)+(1*4)=63
63 % 10 = 3
So 69-44-3 is a valid CAS Registry Number.
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
69-44-3Relevant articles and documents
Continuous preparing method for amodiaquine hydrochloride
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Paragraph 0027, (2016/10/27)
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.