ChemicalBook--->CAS DataBase List--->69-44-3

69-44-3

69-44-3 Structure

69-44-3 Structure
IdentificationBack Directory
[Name]

Acrichin dihydrochloride
[CAS]

69-44-3
[Synonyms]

AMODIAQUINE HCL
camoquinhydrochloride
Acrichin dihydrochloride
AMODIAQUIN HYDROCHLORIDE
AMODIAQUINE HYDROCHLORIDE
AMODIAQUIN DIHYDROCHLORIDE
AMODIAQUINE DIHYDROCHLORIDE
BULK DRUG : AMODIAQUINE HYDROCHLORIDE (DMF GRADE)
4-((7-chloro-4-quinolyl)amino)-alpha-(diethylamino)-o-cresodihydrochloride
4-((7-chloro-4-quinolyl)amino)-alpha-(diethylamino)-o-cresoldihydrochloride
4-[(7-chloro-4-quinolyl)amino]-2-(diethylaminomethyl)phenol dihydrochloride
4-[(7-Chloroquinolin-4-yl)amino]-2-(diethylaminomethyl)phenol dihydrochloride
7-Chloro-4-(3'-diethylaminomethyl-4'-hydroxyanilino)quinoline dihydrochloride
4-[(7-CHLORO-4-QUINOLINYL)AMINO]-2-[(DIETHYLAMINO)METHYL]PHENOL DIHYDROCHLORIDE
[EINECS(EC#)]

200-706-0
[Molecular Formula]

C20H24Cl3N3O
[MDL Number]

MFCD00078857
[MOL File]

69-44-3.mol
[Molecular Weight]

428.78
Chemical PropertiesBack Directory
[storage temp. ]

Sealed in dry,Room Temperature
[solubility ]

DMSO: 125 mg/mL (291.52 mM)
[form ]

Solid
[color ]

Light yellow to yellow
[InChI]

InChI=1S/C20H22ClN3O.ClH/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);1H
[InChIKey]

KBTNVJNLEFHBSO-UHFFFAOYSA-N
[SMILES]

N(C1C=CC(O)=C(CN(CC)CC)C=1)C1=CC=NC2=CC(Cl)=CC=C12.Cl
Safety DataBack Directory
[Symbol(GHS) ]

Exclamation Mark (GHS07)
GHS07
[Signal word ]

Warning
[Hazard statements ]

H302
[Precautionary statements ]

P264-P270-P301+P312-P330-P501
[WGK Germany ]

3
Hazard InformationBack Directory
[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
[References]

[1] Patent: CN105503718, 2016, A. Location in patent: Paragraph 0027
Spectrum DetailBack Directory
[Spectrum Detail]

Acrichin dihydrochloride(69-44-3)1HNMR
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