4-[(7-Chloroquinolin-4-yl)amino]-2-[(diethylammonio)methyl]phenolate

Base Information

• Chemical Name: 4-[(7-Chloroquinolin-4-yl)amino]-2-[(diethylammonio)methyl]phenolate
• CAS No.: 86-42-0
• Molecular Formula: C20H22ClN3O
• Molecular Weight: 355.867
• Hs Code.: 2933499090
• Mol file: 86-42-0.mol

Synonyms:4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylammonio)methyl]phenolate;4-[(7-chloroquinolin-4-yl)amino]-2-[(diethylazaniumyl)methyl]phenolate;STK564133;AKOS005489570

Chemical Property of 4-[(7-Chloroquinolin-4-yl)amino]-2-[(diethylammonio)methyl]phenolate

Chemical Property:

• Appearance/Colour: cyrstalline solid
• Melting Point: 208 °C
• Boiling Point: 478 °C at 760 mmHg
• PKA: 9.43±0.50(Predicted)
• Flash Point: 242.9 °C
• PSA: 48.39000
• Density: 1.258 g/cm³
• LogP: 5.25220
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly, Sonicated), Methanol (Slightly)
• XLogP3: 3.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 355.1451400
• Heavy Atom Count: 25
• Complexity: 406

Purity/Quality:

99% ^*data from raw suppliers

Amodiaquine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC[NH+](CC)CC1=C(C=CC(=C1)NC2=C3C=CC(=CC3=NC=C2)Cl)[O-]
• Description: Amodiaquine is a prodrug form of the antimalarial compound N-desethyl amodiaquine . It is active against several strains of P. falciparum in vitro (EC50s = 0.23-0.52 nM) and exhibits a synergistic effect when used in combination with N-desethyl amodiaquine. Amodiaquine dose-dependently inhibits development of parasitemia in a mouse model of P. berghei infection.
• Uses: An antimalarial
• Indications: Amodiaquine (Camoquin) is another 4-aminoquinoline derivative whose antimalarial spectrum and adverse reactions are similar to those of chloroquine, although chloroquine-resistant parasites may not be amodiaquine- resistant to the same degree. Prolonged treatment with amodiaquine may result in pigmentation of the palate, nail beds, and skin. There is a 1:2000 risk of agranulocytosis and hepatocellular dysfunction when the drug is used prophylactically.
• Clinical Use: Treatment of falciparum malaria Mechanistically, it is very similar to chloroquine and does nothave any advantages over the other 4-aminoquinoline drugs.When used for prophylaxis of malaria, it had a higher incidenceof hepatitis and agranulocytosis than that was chloroquine.There is evidence that the hydroquinone (phenol)amine system readily oxidizes to a quinone imine either autoxidatively and/or metabolically, and this productmay contribute to amodiaquine’s toxicity.

Technology Process of 4-[(7-Chloroquinolin-4-yl)amino]-2-[(diethylammonio)methyl]phenolate

There total 7 articles about 4-[(7-Chloroquinolin-4-yl)amino]-2-[(diethylammonio)methyl]phenolate 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:

4,7-dichloroquinoline (86-98-6,1138471-54-1) + 4-amino-phenol (123-30-8) + diethylamine (109-89-7) → amodiaquin (86-42-0)

Guidance literature:

4,7-dichloroquinoline; 4-amino-phenol; With acetic acid; In water; at 20 - 110 ℃; for 1h;

diethylamine; With formaldehyd; In water; acetic acid; at 50 ℃; for 4h;

With hydrogenchloride; In water;

Reference yield:

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide (121-78-8) → amodiaquin (86-42-0)

Guidance literature:

With hydrogenchloride; Erwaermen des Reaktionsprodukts mit 4,7-Dichlor-chinolin;

DOI:10.1021/ja01184a023

Reference yield:

4-acetaminophenol (103-90-2,8055-08-1) → amodiaquin (86-42-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂O

2: aq. HCl

With hydrogenchloride; In water;

DOI:10.1021/jm00035a017

upstream raw materials:

N-{3-[(diethylamino)methyl]-4-hydroxyphenyl}acetamide

formaldehyd

diethylamine

4,7-dichloroquinoline

Downstream raw materials:

N-desethylamodiaquine

4-(7'-chloroquinolin-4'-ylamino)-2,6-bis(diethylaminomethyl)phenol

Refernces

• 1、 O'Neill, Paul M.,Harrison, Anthony C.,Storr, Richard C.,Hawley, Shaun R.,Ward, Stephen A.,Park, B. Kevin. "The Effect of Fluorine Substitution on the Metabolism and Antimalarial Activity of Amodiaquine". . p. 1362 - 1370. Retrieved 2007/10/02.
• 2、 Natarajan,Ngiam Tong Lan. "An alternative method for the synthesis of camoquine.". . p. 1230 - 1231. Retrieved 2007/10/04.