Ethyl 4-chloro-6-fluoroquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-chloro-6-fluoroquinoline-3-carboxylate
• CAS No.: 77779-49-8
• Molecular Formula: C12H9ClFNO2
• Molecular Weight: 253.66
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID30363155
• Wikidata: Q72473615
• Mol file: 77779-49-8.mol

Synonyms:ethyl 4-chloro-6-fluoroquinoline-3-carboxylate;77779-49-8;4-Chloro-6-fluoroquinoline-3-carboxylic acid ethyl ester;ETHYL4-CHLORO-6-FLUOROQUINOLINE-3-CARBOXYLATE;Oprea1_272552;SCHEMBL538191;DTXSID30363155;AMY10629;BBL028330;MFCD00173350;STL239374;AKOS000189955;SB68935;BP-20307;CS-0071054;FT-0730302;ethyl 4-chloro-6-fluoroquinolin-3-carboxylate;5J-038;EN300-110488;ethyl 6-chloro-4-fluoroquinoline-3-carboxylate;Ethyl 4-chloro-6-fluoro-quinoline-3-carboxylate;4chloro-6-fluoro-quinoline-3-carboxylic acid ethyl ester;F2156-0059;4-Chloro-6-fluoro-quinoline-3-carboxylic acid ethyl ester;Ethyl 4-chloro-6-fluoroquinoline-3-carboxylate, AldrichCPR

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

Chemical Property:

• Vapor Pressure: 0.00015mmHg at 25°C
• Melting Point: 62-63℃
• Refractive Index: 1.593
• Boiling Point: 332.1 °C at 760 mmHg
• Flash Point: 154.6 °C
• PSA: 39.19000
• Density: 1.354 g/cm3
• LogP: 3.20400
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 3.1
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 253.0305844
• Heavy Atom Count: 17
• Complexity: 290

Purity/Quality:

99% ^*data from raw suppliers

Ethyl 4-chloro-6-fluoroquinoline-3-carboxylate Aldrich ^*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)F

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

There total 8 articles about Ethyl 4-chloro-6-fluoroquinoline-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: 100.0%

ethyl 6-fluoro-4-hydroxy-3-quinoline-carboxylate (318-35-4) → 4-chloro-6-fluoroquinoline-3-carboxylic acid ethyl ester (77779-49-8)

Guidance literature:

ethyl 6-fluoro-4-hydroxy-3-quinoline-carboxylate; With trichlorophosphate; at 100 ℃; for 0.5h;

With ammonia; In water; at 0 ℃;

Reference yield: 89.0%

ethyl 6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylate (71083-00-6) → 4-chloro-6-fluoroquinoline-3-carboxylic acid ethyl ester (77779-49-8)

Guidance literature:

With thionyl chloride; for 3h; Heating / reflux;

Reference yield:

diethyl 2-(4-fluoroanilino)methylenemalonate (26832-96-2) → 4-chloro-6-fluoroquinoline-3-carboxylic acid ethyl ester (77779-49-8)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl ether / 1 h / 250 °C

2: 0.995 g / thionyl chloride / 1 h / 80 °C

With thionyl chloride; In diphenylether;

DOI:10.1021/jm060262x

upstream raw materials:

ethyl 6-fluoro-4-hydroxy-3-quinoline-carboxylate

diethyl 2-(4-fluoroanilino)methylenemalonate

diethyl 2-ethoxymethylenemalonate

4-fluoroaniline

Downstream raw materials:

ethyl 4-((R)-1-(dimethylcarbamoyl)-3-(phenylthio)propan-2-ylamino)-6-fluoro quinoline-3-carboxylate

(E)-ethyl 4-([1,1'-biphenyl]-4-ylimino)-6-fluoro-1-methyl-1,4-dihydroquinoline-3-carboxylate

(E)-ethyl 4-([1,1'-biphenyl]-4-ylimino)-1-ethyl-6-fluoro-1,4-dihydroquinoline-3-carboxylate

Refernces

• 1、 Medapi, Brahmam,Suryadevara, Priyanka,Renuka, Janupally,Sridevi, Jonnalagadda Padma,Yogeeswari, Perumal,Sriram, Dharmarajan. "4-Aminoquinoline derivatives as novel Mycobacterium tuberculosis GyrB inhibitors: Structural optimization, synthesis and biological evaluation". . p. 1 - 16. Retrieved 2015/09/02.
• 2、 Goncalves, Victor,Brannigan, James A.,Whalley, David,Ansell, Keith H.,Saxty, Barbara,Holder, Anthony A.,Wilkinson, Anthony J.,Tate, Edward W.,Leatherbarrow, Robin J.. "Discovery of plasmodium vivax N -myristoyltransferase inhibitors: Screening, synthesis, and structural characterization of their binding mode". supporting information; experimental part. p. 3578 - 3582. Retrieved 2012/06/01.