Ethyl 4,7-dichloroquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 4,7-dichloroquinoline-3-carboxylate
• CAS No.: 19499-19-5
• Molecular Formula: C12H9 Cl2 N O2
• Molecular Weight: 270.115
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID20482703
• Wikidata: Q82319316
• Mol file: 19499-19-5.mol

Synonyms:ETHYL 4,7-DICHLOROQUINOLINE-3-CARBOXYLATE;19499-19-5;SCHEMBL1178069;DTXSID20482703;KWYQZEQRIMVMTH-UHFFFAOYSA-N;AKOS005209009;SB68647;ethyl-4,7-dichloroquinoline-3-carboxylate;CS-0333721;FT-0729152;A905009;4,7-dichloro-3-Quinolinecarboxylic acid ethyl ester;4,7-Dichloro-quinoline-3-carboxylic acid ethyl ester;4,7-Dichloroquinoline-3-carboxylic acid, ethyl ester;4,5,6,7-TETRAHYDRO-2-BENZOTHIOPHENE-1-CARBOXYLICACID

Chemical Property of Ethyl 4,7-dichloroquinoline-3-carboxylate

Chemical Property:

• Melting Point: 80-82 °C
• Boiling Point: 360.0±37.0 °C(Predicted)
• PKA: 0.23±0.38(Predicted)
• PSA: 39.19000
• Density: 1.384±0.06 g/cm3(Predicted)
• LogP: 3.71830
• XLogP3: 3.7
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 269.0010339
• Heavy Atom Count: 17
• Complexity: 288

Purity/Quality:

98%min ^*data from raw suppliers

Ethyl4,7-dichloroquinoline-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CN=C2C=C(C=CC2=C1Cl)Cl
• Uses: ethyl 4,7-dichloroquinoline-3-carboxylate used in the preparartion of antitumor activities and SAR of (morpholine)carbonyl- and (ethoxycarbonyl)anilinoqunolines which are useful in the treatment of cancer.

Technology Process of Ethyl 4,7-dichloroquinoline-3-carboxylate

There total 10 articles about Ethyl 4,7-dichloroquinoline-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: 75.56%

7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester (16600-22-9) → 4,7-dichloroquinoline-3-carboxylic acid ethyl ester (19499-19-5)

Guidance literature:

With trichlorophosphate; at 110 ℃; for 3h;

Reference yield: 73.0%

ethyl 7-chloro-1,4-dihydro-4-oxo-3-quinolinecarboxylate (54132-35-3) → 4,7-dichloroquinoline-3-carboxylic acid ethyl ester (19499-19-5)

Guidance literature:

With trichlorophosphate; for 2h; Reflux;

DOI:10.1016/j.bmc.2019.06.006

Reference yield:

3-chloro-aniline (108-42-9) → 4,7-dichloroquinoline-3-carboxylic acid ethyl ester (19499-19-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine / toluene / 2 h / Heating

2.1: diphenyl ether / 1 h / 250 °C

2.2: 350 mg / thionyl chloride / 1 h / 80 °C

With pyridine; In diphenylether; toluene;

DOI:10.1021/jm060262x

upstream raw materials:

7-chloro-4-hydroxyquinoline-3-carboxylic acid,ethyl ester

2-(3-chlorophenylamino)methylenemalonic acid diethyl ester

3-chloro-aniline

diethyl 2-ethoxymethylenemalonate

Downstream raw materials:

C₁₆H₁₆ClN₃O

ethyl 2-([1,1'-biphenyl]-3-yl)-7-chloro-4-oxo-1,4-dihydroquinoline-3-carboxylate

4,7-dichloroquinoline-3-carboxylic acid

8-chloro[1,2,3]triazino[5,4-c]quinolin-4-ol

Refernces

• 1、 Simeone,Iorio,Siebert,Rehman,Schnürch,Mihovilovic,Ernst. "Defined concatenated α6α1β3γ2 GABAA receptor constructs reveal dual action of pyrazoloquinolinone allosteric modulators". . p. 3167 - 3178. Retrieved 2019/06/17.
• 2、 Zhang, Yiqun,Clark, Julie A.,Connelly, Michele C.,Zhu, Fangyi,Min, Jaeki,Guiguemde, W. Armand,Pradhan, Anupam,Iyer, Lalitha,Furimsky, Anna,Gow, Jason,Parman, Toufan,El Mazouni, Farah,Phillips, Margaret A.,Kyle, Dennis E.,Mirsalis, Jon,Guy, R. Kiplin. "Lead optimization of 3-carboxyl-4(1 H)-quinolones to deliver orally bioavailable antimalarials". . p. 4205 - 4219. Retrieved 2012/07/02.