Amodiaquin (dihydrochloride)

Base Information

• Chemical Name: Amodiaquin (dihydrochloride)
• CAS No.: 69-44-3
• Molecular Formula: C₂₀H₂₄ClN₃O*2Cl
• Molecular Weight: 428.789
• Hs Code.: 2933499090
• European Community (EC) Number: 200-706-0
• ChEMBL ID: CHEMBL1630
• NCI Thesaurus Code: C65232
• Mol file: 69-44-3.mol

Synonyms:Amodiachin;Amodiaquin;Amodiaquine;Amodiaquine Hydrochloride;Camoquin;Camoquine;Flavoquine;Hydrochloride, Amodiaquine

Chemical Property of Amodiaquin (dihydrochloride)

Chemical Property:

• Boiling Point: 478 °C at 760 mmHg
• Flash Point: 242.9 °C
• PSA: 48.39000
• LogP: 6.05420
• Storage Temp.: Sealed in dry,Room Temperature
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 6
• Exact Mass: 391.1218178
• Heavy Atom Count: 26
• Complexity: 406

Purity/Quality:

99% ^*data from raw suppliers

4-((7-Chloroquinolin-4-yl)amino)-2-((diethylamino)methyl)phenolDihydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)CC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)O.Cl
• Uses: Medicine (antimalarial).
• Therapeutic Function: Antimalarial

Technology Process of Amodiaquin (dihydrochloride)

There total 3 articles about Amodiaquin (dihydrochloride) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 71.0%

4,7-dichloroquinoline (86-98-6,1138471-54-1) + 4-amino-2-((diethylamino)methyl)phenol (51387-92-9) → amodiaquine hydrochloride (69-44-3,118490-14-5)

Guidance literature:

With indium(III) chloride; In acetonitrile; at 120 ℃; for 2h; regioselective reaction; Microwave irradiation;

DOI:10.1002/adsc.201400674

Reference yield:

4,7-dichloroquinoline (86-98-6,1138471-54-1) + 4-amino-2-((diethylamino)methyl)phenol (51387-92-9) → amodiaquine hydrochloride (69-44-3,118490-14-5)

Guidance literature:

With sodium hydroxide; at 100 ℃; for 1h; pH=3; Temperature; pH-value; Reagent/catalyst;

Reference yield:

4-acetaminophenol (103-90-2,8055-08-1) → amodiaquine hydrochloride (69-44-3,118490-14-5)

Guidance literature:

Multi-step reaction with 3 steps

1: water / 0.5 h / 80 °C

2: hydrogenchloride / water / 2 h / 104 °C

3: sodium hydroxide / 1 h / 100 °C / pH 3

With hydrogenchloride; sodium hydroxide; In water; 1: |Mannich Aminomethylation;

upstream raw materials:

4-acetaminophenol

4,7-dichloroquinoline

4-amino-2-((diethylamino)methyl)phenol

Downstream raw materials:

VO⁽²⁺⁾*(C₂H₅)2NCH₂C₆H₃OHNHC₉H₅NCl*SO₄^(2-)=VO(C₂H₅)2NCH₂C₆H₃OHNHC₉H₅NClSO₄

4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylamino)methyl]phenol tetrachlorocobaltate(II) salt

Refernces

• 1、 Staderini, Matteo,Bolognesi, Maria Laura,Menndez, J. Carlos. "Lewis acid-catalyzed generation of C-C and C-N bonds on π-deficient heterocyclic substrates". supporting information. p. 185 - 195. Retrieved 2015/01/30.