Diethyl 2,3-quinolinedicarboxylate

Base Information

• Chemical Name: Diethyl 2,3-quinolinedicarboxylate
• CAS No.: 32413-08-4
• Molecular Formula: C15H15NO4
• Molecular Weight: 273.288
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID10446955
• Nikkaji Number: J107.350H
• Wikidata: Q72462183
• Mol file: 32413-08-4.mol

Synonyms:32413-08-4;Diethyl 2,3-quinolinedicarboxylate;Diethyl Quinoline-2,3-dicarboxylate;Quinoline-2,3-dicarboxylic acid diethyl ester;diethylquinoline-2,3-dicarboxylate;Quinoline-2,3-dicarboxylic acid diethylester;SCHEMBL8582386;DTXSID10446955;ICMBEQVDQPLOFB-UHFFFAOYSA-N;Diethyl?quinoline-2,3-dicarboxylate;MFCD08063364;AKOS015854388;AB43492;AC-8378;FT-0639020;A821265;2,3-QUINOLINEDICARBOXYLIC ACID DIETHYL ESTER

Chemical Property of Diethyl 2,3-quinolinedicarboxylate

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 1.11E-05mmHg at 25°C
• Melting Point: 54-56°C
• Refractive Index: 1.579
• Boiling Point: 370.4 °C at 760 mmHg
• PKA: 0.20±0.50(Predicted)
• Flash Point: 177.8 °C
• PSA: 65.49000
• Density: 1.211g/cm³
• LogP: 2.58820
• XLogP3: 3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 273.10010796
• Heavy Atom Count: 20
• Complexity: 358

Purity/Quality:

99% ^*data from raw suppliers

Diethylquinoline-2,3-dicarboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CC2=CC=CC=C2N=C1C(=O)OCC

Technology Process of Diethyl 2,3-quinolinedicarboxylate

There total 17 articles about Diethyl 2,3-quinolinedicarboxylate 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: 86.0%

2-nitro-benzaldehyde (552-89-6) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl quinoline-2,3-dicarboxylate (32413-08-4)

Guidance literature:

With indium(III) chloride; tin(II) chloride dihdyrate; In ethanol; for 3.5h; regioselective reaction; Reflux;

DOI:10.1002/asia.201100872

Reference yield: 83.7%

anilino-fumarate → diethyl quinoline-2,3-dicarboxylate (32413-08-4)

Guidance literature:

With trichlorophosphate; In N-methyl-acetamide; water; toluene;

Reference yield: 76.0%

o-aminobenzaldehyde (529-23-7) + acetylenedicarboxylic acid diethyl ester (762-21-0) → diethyl quinoline-2,3-dicarboxylate (32413-08-4)

Guidance literature:

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

DOI:10.1016/j.jcat.2020.01.034

upstream raw materials:

o-aminobenzaldehyde

diethyl oxaloacetate

Diethyl Quinoline-2,3-dicarboxylate N-Oxide

acetylenedicarboxylic acid diethyl ester

Downstream raw materials:

2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-Yl]-3-quinolinecarboxylic acid

potassium salt of 2-(5-isopropyl-5-methyl-4-oxoimidazolin-2-yl)-3-quinolinecarboxylic acid

quinoline-2,3-dicarboxylic acid

quinoline-2,3-dicarboxylic acid diamide

Refernces

• 1、 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 1984.
• 2、 Xia, Xiao-Feng,He, Wei,Wang, Dawei. "Metal-Free Oxidative Annulation/Cyclization of 1,6-Enynes for the Synthesis of 4-Carbonylquinolines". supporting information. p. 2959 - 2964. Retrieved 2019/04/30.
• 3、 Chanda, Tanmoy,Verma, Rajiv Kumar,Singh, Maya Shankar. "InCl3-driven regioselective synthesis of functionalized/ annulated quinolines: Scope and limitations". supporting information; experimental part. p. 778 - 787. Retrieved 2012/06/29.