6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester

Base Information

• Chemical Name: 6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester
• CAS No.: 92525-74-1
• Molecular Formula: C₁₅H₁₄ClNO₄
• Molecular Weight: 307.733
• Hs Code.: 2933499090
• European Community (EC) Number: 804-516-4
• DSSTox Substance ID: DTXSID40537946
• Wikidata: Q82413124
• Mol file: 92525-74-1.mol

Synonyms:92525-74-1;6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester;Diethyl 6-chloroquinoline-2,3-dicarboxylate;SCHEMBL10665205;DTXSID40537946;MFCD09787825;AB52323;CS-0367390;6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester, AldrichCPR

Chemical Property of 6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester

Chemical Property:

• Vapor Pressure: 1.4E-06mmHg at 25°C
• Boiling Point: 399.1oC at 760 mmHg
• Flash Point: 195.2oC
• PSA: 65.49000
• Density: 1.295g/cm3
• LogP: 3.24160
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 307.0611356
• Heavy Atom Count: 21
• Complexity: 390

Purity/Quality:

98%min ^*data from raw suppliers

6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N=C2C=CC(=CC2=C1)Cl)C(=O)OCC

Technology Process of 6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester

There total 5 articles about 6-Chloroquinoline-2,3-dicarboxylic acid diethyl ester 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: 91.0%

2-amino-5-chlorobenzaldehyde (20028-53-9) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 6-chloroquinoline-2,3-dicarboxylate (92525-74-1)

Guidance literature:

With β‐cyclodextrin; In water; at 65 - 75 ℃; for 6h;

DOI:10.1002/hlca.200900254

Reference yield: 75.0%

5-chloro-2-nitrobenzaldehyde (6628-86-0) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl 6-chloroquinoline-2,3-dicarboxylate (92525-74-1)

Guidance literature:

With formic acid; at 110 ℃; for 18h; Inert atmosphere;

DOI:10.1016/j.jcat.2020.01.034

Reference yield: 47.0%

diethyl-6-chloroquinoline-2,3-dicarboxylate N-oxide (92525-69-4) → diethyl 6-chloroquinoline-2,3-dicarboxylate (92525-74-1)

Guidance literature:

With phosphorus trichloride; In chloroform; for 3h; Heating;

DOI:10.1021/jo00199a050

upstream raw materials:

diethyl-6-chloroquinoline-2,3-dicarboxylate N-oxide

diethyl 2-(diethoxyphosphoryl)succinate

5-chloro-2-nitrobenzaldehyde

2-amino-5-chlorobenzaldehyde

Refernces

• 1、 Venkanna, Avudoddi,Swapna, Kokkirala,Rao, Pallapothula Venkateswar. "Recyclable nano copper oxide catalyzed synthesis of quinoline-2,3- dicarboxylates under ligand free conditions". . p. 15154 - 15160. Retrieved 2014/04/17.
• 2、 Kadin, Saul B.,Lamphere, Charles H.. "Reaction of 2-Nitrobenzaldehydes with Diethyl (Diethoxyphosphinyl)succinate: A New Synthesis of Quinoline-2,3-dicarboxylic Acid Esters via Their N-Oxides". . p. 4999 - 5000. Retrieved 2007/10/02.