Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate

Base Information

• Chemical Name: Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate
• CAS No.: 27568-04-3
• Molecular Formula: C₁₃H₁₃NO₄
• Molecular Weight: 247.251
• Hs Code.: 29334900
• European Community (EC) Number: 803-472-3
• NSC Number: 196905
• DSSTox Substance ID: DTXSID80950236
• Wikidata: Q72475236
• Mol file: 27568-04-3.mol

Synonyms:Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate;27568-04-3;71082-34-3;Ethyl 8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate;AURORA 17729;8-Methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid ethyl ester;4-Hydroxy-8-methoxyquinoline-3-carboxylic acid ethyl ester;ethyl 8-methoxy-4-oxo-1H-quinoline-3-carboxylate;MFCD01829412;4-Hydroxy-8-methoxy-quinoline-3-carboxylic acid ethyl ester;NSC196905;Oprea1_108159;Oprea1_177673;Oprea1_292837;SCHEMBL774558;DTXSID80950236;Ethyl 1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylate;HCYNWEIHLHVPEW-UHFFFAOYSA-N;3-Quinolinecarboxylic acid, 4-hydroxy-8-methoxy-, ethyl ester;AMY26553;SMSF0009127;WCA08234;BBL028333;MFCD00173382;STL372954;STL519498;AKOS000655529;AKOS002285124;AB04332;CB00074;CCG-105904;CS-W014634;NSC-196905;SB69491;BP-20285;BB 0222252;CS-0368421;FT-0638713;EN300-97608;6J-018;C74432;A850636;SR-01000425947;J-515512;J-650044;SR-01000425947-1;Ethyl8-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylate;F0914-1307;Z1723549307;3-Quinolinecarboxylicacid,4-hydroxy-8-methoxy-,ethyl ester;4-Hydroxy-8-methoxy-quinoline-3-carboxylic acid ethyl ester;1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acid ethyl ester;4-Hydroxy-8-methoxyquinoline-3-carboxylic acid ethyl ester, AldrichCPR

Chemical Property of Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate

Chemical Property:

• Vapor Pressure: 2.46E-06mmHg at 25°C
• Boiling Point: 391.5°Cat760mmHg
• PKA: 2.72±0.50(Predicted)
• Flash Point: 190.6°C
• PSA: 68.65000
• Density: 1.247g/cm³
• LogP: 2.12570
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 247.08445790
• Heavy Atom Count: 18
• Complexity: 377

Purity/Quality:

97% ^*data from raw suppliers

Ethyl4-hydroxy-8-methoxyquinoline-3-carboxylate ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=CNC2=C(C1=O)C=CC=C2OC

Technology Process of Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate

There total 6 articles about Ethyl 4-hydroxy-8-methoxyquinoline-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: 64.0%

2-[(2-methoxyphenylamino)-methylene]-malonic acid diethyl ester (104007-09-2) → Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate (27568-04-3)

Guidance literature:

In diphenyl ether-biphenyl eutectic; at 250 ℃;

Reference yield:

2-[(2-methoxyphenylamino)-methylene]-malonic acid diethyl ester (104007-09-2) + diethyl 2-ethoxymethylenemalonate (87-13-8) → Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate (27568-04-3)

Guidance literature:

With dowtherm A; at 260 ℃; for 0.5h;

DOI:10.3390/molecules21010021

Reference yield:

diethyl 2-ethoxymethylenemalonate (87-13-8) → Ethyl 4-hydroxy-8-methoxyquinoline-3-carboxylate (27568-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol / Reflux

2: dowtherm A / 0.5 h / 260 °C

With dowtherm A; In ethanol;

DOI:10.3390/molecules21010021

upstream raw materials:

2-methoxy-phenylamine

diethyl 2-ethoxymethylenemalonate

2-[(2-methoxyphenylamino)-methylene]-malonic acid diethyl ester

Downstream raw materials:

4-hydroxy-8-methoxyquinoline-3-carboxylic acid

4-hydroxy-8-methoxy-quinoline-3-carboxylic acid hydrazide

N-(β-phenethyl)-4-hydroxy-8-methoxyquinoline-3-carboxamide

4-Chloro-8-methoxyquinoline-3-carboxylic acid ethyl ester

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