Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate
• CAS No.: 22931-71-1
• Molecular Formula: C13H12ClNO3
• Molecular Weight: 265.696
• Hs Code.: 2933499090
• European Community (EC) Number: 803-412-6
• NSC Number: 196908
• DSSTox Substance ID: DTXSID30307938
• Wikidata: Q72473669
• ChEMBL ID: CHEMBL601324
• Mol file: 22931-71-1.mol

Synonyms:ethyl 4-chloro-6-methoxyquinoline-3-carboxylate;22931-71-1;4-Chloro-6-methoxyquinoline-3-carboxylic acid ethyl ester;GNF-Pf-3551;MFCD00173417;Ethyl4-chloro-6-methoxyquinoline-3-carboxylate;Ethyl 4-chloro-6-methoxy-quinoline-3-carboxylate;NSC196908;Oprea1_016451;SCHEMBL544894;CHEMBL601324;DTXSID30307938;TQR0654;3-Quinolinecarboxylic acid, 4-chloro-6-methoxy-, ethyl ester;STL331620;AKOS000181060;CCG-108125;NSC-196908;SB71655;3-Carbethoxy-4-chloro-6-methoxyquinoline;4-chloro-3-ethoxycarbonyl-6-methoxyquinoline;6-methoxy-4-chloro-3-ethoxycarbonylquinoline;AM20050972;CS-0099666;EU-0073812;FT-0646041;ethyl 4chloro-6methoxyquinoline-3-carboxylate;6J-071;EN300-110495;ethyl 4-chloro-6-methoxyquinolin-3-carboxylate;A878382;Ethyl 4-chloro-6-methoxy-3-quinolinecarboxylate #;SR-01000453170;J-520994;SR-01000453170-1;4-Chloro-6-methoxyquinoline-3-carboxylic acid ethyl ester, AldrichCPR

Chemical Property of Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.42E-05mmHg at 25°C
• Melting Point: 88-90℃
• Refractive Index: 1.592
• Boiling Point: 366.9 °C at 760 mmHg
• Flash Point: 175.7 °C
• PSA: 48.42000
• Density: 1.282 g/cm³
• LogP: 3.07350
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 265.0505709
• Heavy Atom Count: 18
• Complexity: 300

Purity/Quality:

99% ^*data from raw suppliers

4-Chloro-6-methoxyquinoline-3-carboxylic acid ethyl ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C2C=CC(=CC2=C1Cl)OC
• Uses: Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate is an important organic intermediate. It can be used in agrochemical, pharmaceutical and dyestuff field.

Technology Process of Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate

There total 10 articles about Ethyl 4-chloro-6-methoxyquinoline-3-carboxylate 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: 98.0%

ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate (77156-78-6) → ethyl 4-chloro-6-methoxyquinolin-3-carboxylate (22931-71-1)

Guidance literature:

With trichlorophosphate; for 2h; Inert atmosphere; Reflux;

DOI:10.1016/j.tetlet.2017.01.042

Reference yield: 98.0%

ethyl 6-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylate (53976-97-9) → ethyl 4-chloro-6-methoxyquinolin-3-carboxylate (22931-71-1)

Guidance literature:

With thionyl chloride; Reflux;

DOI:10.1016/j.bmc.2018.06.021

Reference yield: 61.0%

diethyl 2-(((4-methoxyphenyl)amino)methylene)malonate (83507-70-4) → ethyl 4-chloro-6-methoxyquinolin-3-carboxylate (22931-71-1)

Guidance literature:

diethyl 2-(((4-methoxyphenyl)amino)methylene)malonate; With trichlorophosphate; at 25 - 100 ℃; for 5h; Heating / reflux;

With sodium hydroxide; In dichloromethane; water; at 25 - 30 ℃; for 1.5h; pH=7.5 - 8;

upstream raw materials:

ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate

diethyl 2-(((4-methoxyphenyl)amino)methylene)malonate

4-methoxy-aniline

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

6-methoxyquinoline-3-carboxylic acid

3-amino-6-methoxyquinoline

4-chloro-3-fluoro-6-methoxyquinoline

ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate

Refernces

• 1、 Sch?fer, Gabriel,Fleischer, Tony,Blumer, Nicole,Udry, Megan,Reber, Stefan,Stansfield, Ian,Liu, Yuanhua,Li, Yan,Li, Pixu. "Initial Route Scouting and Final Process Development for the Multi-Kg Production of 3-Fluoro-6-methoxyquinoline from p-Anisidine and 2-Fluoromalonic Acid". . p. 347 - 357. Retrieved 2022/02/01.
• 2、 Al-Sanea, Mohammad M.,Elkamhawy, Ahmed,Paik, Sora,Bua, Silvia,Ha Lee, So,Abdelgawad, Mohamed A.,Roh, Eun Joo,Eldehna, Wagdy M.,Supuran, Claudiu T.. "Synthesis and biological evaluation of novel 3-(quinolin-4-ylamino)benzenesulfonamidesAQ3 as carbonic anhydrase isoforms I and II inhibitors". . p. 1457 - 1464. Retrieved 2019/08/26.