Ethyl 4-chloro-8-cyanoquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-chloro-8-cyanoquinoline-3-carboxylate
• CAS No.: 77173-67-2
• Molecular Formula: C₁₃H₉ClN₂O₂
• Molecular Weight: 260.68
• Hs Code.: 2933990090
• European Community (EC) Number: 678-654-7
• DSSTox Substance ID: DTXSID80396054
• Wikidata: Q82196530
• Mol file: 77173-67-2.mol

Synonyms:ethyl 4-chloro-8-cyanoquinoline-3-carboxylate;77173-67-2;Ethyl4-chloro-8-cyanoquinoline-3-carboxylate;Oprea1_224462;SCHEMBL528517;DTXSID80396054;MFCD00173414;AKOS005097194;SB68737;s10356;A9774;FT-0757666;6J-063;4-Chloro-8-cyanoquinoline-3-carboxylic acid ethyl este;ETHYL 4-CHLORO-8-CYANOQUINOXALINE-3-CARBOXYLATE

Chemical Property of Ethyl 4-chloro-8-cyanoquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 1.5E-06mmHg at 25°C
• Refractive Index: 1.624
• Boiling Point: 398.2 °C at 760 mmHg
• Flash Point: 194.6 °C
• PSA: 62.98000
• Density: 1.37 g/cm³
• LogP: 2.93658
• Storage Temp.: 2-8°C
• Sensitive.: Air Sensitive
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 260.0352552
• Heavy Atom Count: 18
• Complexity: 365

Purity/Quality:

99% ^*data from raw suppliers

Ethyl4-chloro-8-cyanoquinoline-3-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C2=CC=CC(=C2N=C1)C#N)Cl

Technology Process of Ethyl 4-chloro-8-cyanoquinoline-3-carboxylate

There total 3 articles about Ethyl 4-chloro-8-cyanoquinoline-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: 80.0%

8-cyano-3-ethoxycarbonyl-1,4-dihydro-4-oxoquinolone (127285-75-0) → 4-chloro-8-cyano-quinoline-3-carboxylic acid ethyl ester (77173-67-2)

Guidance literature:

With thionyl chloride;

DOI:10.1016/j.bmcl.2006.07.006

Reference yield:

diethyl 2-ethoxymethylenemalonate (87-13-8) → 4-chloro-8-cyano-quinoline-3-carboxylic acid ethyl ester (77173-67-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / diphenyl ether / 250 °C

2: 80 percent / SOCl₂

With thionyl chloride; In diphenylether; 1: Gould-Jacobs condensation;

DOI:10.1016/j.bmcl.2006.07.006

Reference yield:

anthranilic acid nitrile (1885-29-6) → 4-chloro-8-cyano-quinoline-3-carboxylic acid ethyl ester (77173-67-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 60 percent / diphenyl ether / 250 °C

2: 80 percent / SOCl₂

With thionyl chloride; In diphenylether; 1: Gould-Jacobs condensation;

DOI:10.1016/j.bmcl.2006.07.006

upstream raw materials:

8-cyano-3-ethoxycarbonyl-1,4-dihydro-4-oxoquinolone

diethyl 2-ethoxymethylenemalonate

anthranilic acid nitrile

Downstream raw materials:

8-{[(4'-fluoro-biphenyl-4-carbonyl)-amino]-methyl}-quinoline-3-carboxylic acid ethyl ester

8-({[6-(4-fluoro-phenyl)-pyridine-3-carbonyl]-amino}-methyl)-quinoline-3-carboxylic acid ethyl ester

Refernces