62265-68-3

Basic information

• Product Name: Quinfamide
• Synonyms: quinfamide;QUINTAMIDE;1-(Dichloroacetyl)-6-(2-furoyloxy)-1,2,3,4-tetrahydroquinoline;2-Furancarboxylic acid 1-(dichloroacetyl)-1,2,3,4-tetrahydroquinolin-6-yl ester;Win-40014;1-(Dichloroacetyl)-6-(2-furoyloxy)-1,2,3,4-tetrahydro-6-quinoline;2-Furancarboxylic Acid 1-(2,2-Dichloroacetyl)-1,2,3,4-tetrahydro-6-quinolinyl Ester;AMenide
• CAS NO: 62265-68-3
• Molecular Formula: C₁₆H₁₃Cl₂NO₄
• Molecular Weight: 354.18
• EINECS: 263-478-1
• Product Categories: Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 62265-68-3.mol
• Article Data: 1

Chemical Properties

• Melting Point: 145-146°C
• Boiling Point: 551.3 °C at 760 mmHg
• Flash Point: 287.2 °C
• Appearance: /
• Density: 1.428g/cm³
• Vapor Pressure: 3.37E-12mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• Solubility: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly, Heated)
• PKA: -0.01±0.20(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Quinfamide(CAS DataBase Reference)
• NIST Chemistry Reference: Quinfamide(62265-68-3)
• EPA Substance Registry System: Quinfamide(62265-68-3)

Safety Data

• Hazardous Substances Data: 62265-68-3(Hazardous Substances Data)

Usage

Description

Quinfamide is an amebicide indicated for the one-day treatment of subacute or chronic intestinal amebiasis. It acts by rendering the trophozoites of E. histolytica incapable of propagation.

Chemical Properties

Off-White Solid

Uses

Different sources of media describe the Uses of 62265-68-3 differently. You can refer to the following data:
1. Quinfamide is an anti-amebic agent used to treat tropical parasitic infections.
2. An antiamebic agent, used to treat tropical parasitic infections

Brand name

Amenide (Sterling Winthrop);AMENOX.

InChI:InChI=1/C16H13Cl2NO4/c17-14(18)15(20)19-7-1-3-10-9-11(5-6-12(10)19)23-16(21)13-4-2-8-22-13/h2,4-6,8-9,14H,1,3,7H2

Synthetic route

2-furancarbonyl chloride (527-69-5) + 1-dichloroacetyl-1,2,3,4-tetrahydro-quinolin-6-ol (62265-67-2) + pyrographite (7440-44-0) → quinfamide (62265-68-3)

Conditions	Yield
With acetic acid; triethylamine In methanol; chloroform; ethyl acetate

6-hydroxy-1,2,3,4-tetrahydroquinoline (3373-00-0) → quinfamide (62265-68-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: hexane; chloroform 2: acetic acid; triethylamine / methanol; chloroform; ethyl acetate View Scheme

Upstream product

• 527-69-5 2-furancarbonyl chloride 
• 62265-67-2 1-dichloroacetyl-1,2,3,4-tetrahydro-quinolin-6-ol 
• 7440-44-0 pyrographite 
• 3373-00-0 6-hydroxy-1,2,3,4-tetrahydroquinoline 

Relevant articles and documents

1-(Halogenated-acetyl)-1,2,3,4-tetrahydro-6-quinolinols and esters thereof

Compounds useful as antiamebic agents are 1-(Ac1)-5-R-6-(Ac2 O)-1,2,3,4-tetrahydroquinolines (I), where Ac1 is haloacetyl, dihaloacetyl or trihaloacetyl with halo being chloro or bromo, R is hydrogen, chloro or bromo, and Ac2 is hydrogen, Ac1, alkanoyl having from one to sixteen carbon atoms, benzoyl, 2(or 3)-thenoyl, 2(or 3)-furoyl or N-(lower-alkyl)carbamoyl. Said compounds are prepared: by reacting 1,2,3,4-tetrahydro-6-quinolinol with an acyl halide of the formula Ac1 -halogen to produce 1-(Ac1)-1,2,3,4-tetrahydro-6-quinolinol having formula I where R and Ac2 are each hydrogen, Ac1 is defined as in formula I and halide is chloride or bromide; by reacting said 1-(Ac1)-1,2,3,4-tetrahydro-6-quinolinol with a chlorinating or brominating agent to produce the corresponding 1-(Ac1)-5-chloro(or bromo)-1,2,3,4-tetrahydro-6-quinolinol where Ac1 is defined as in claim 1; and, by reacting 1-(Ac1)-5-R-1,2,3,4-tetrahydro-6-quinolinol with an acylating agent providing Ac2 to produce 1-(Ac1)-5-R-1,2,3,4-tetrahydro-6-(Ac2 O)quinoline having formula I where R is hydrogen, chloro or bromo, Ac1 is defined as in formula I and Ac2 is other than hydrogen as defined in formula I.