Ethyl 4-hydroxyquinoline-2-carboxylate

Base Information

• Chemical Name: Ethyl 4-hydroxyquinoline-2-carboxylate
• CAS No.: 24782-43-2
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• Hs Code.: 2933499090
• European Community (EC) Number: 627-438-0
• NSC Number: 403064,136917
• DSSTox Substance ID: DTXSID90947692
• Wikidata: Q72475378
• Mol file: 24782-43-2.mol

Synonyms:ethyl 4-hydroxyquinoline-2-carboxylate;24782-43-2;Ethyl 4-oxo-1,4-dihydroquinoline-2-carboxylate;13720-90-6;Ethyl 4-hydroxy-2-quinolinecarboxylate;ethyl 4-oxo-1H-quinoline-2-carboxylate;2-Quinolinecarboxylic acid, 4-hydroxy-, ethyl ester;MFCD01863732;NSC136917;Ethyl4-oxo-1,4-dihydroquinoline-2-carboxylate;4-Hydroxy-quinoline-2-carboxylic acid ethyl ester;carbethoxy-4-hydroxyquinoline;SCHEMBL1733527;DTXSID90947692;UACLREXZGKWWIC-UHFFFAOYSA-N;HMS3435F16;AMY31829;4-Hydroxyquinaldic acid, ethyl ester;MFCD11998911;NSC403064;STK503454;AKOS005171528;AKOS016000784;CCG-127125;NSC-136917;NSC-403064;SB68783;SB71473;ethyl-4-hydroxy-quinoline-2-carboxylate;BP-13018;BS-11902;BB 0259465;FT-0646059;Ethyl 4-hydroxy-2-quinolinecarboxylate, 96%;A22148;E85515;4-hydroxy-2-quinolinecarboxylic acid ethyl ester;4-hydroxyquinoline-2-carboxylic acid ethyl ester;A849431;AF-753/00286039;Ethyl 1,4-dihydro-4-oxo-quinoline-2-carboxylate;J-015671;4-Oxo-1,4-dihydroquinoline-2-carboxylic acid ethyl ester

Chemical Property of Ethyl 4-hydroxyquinoline-2-carboxylate

Chemical Property:

• Vapor Pressure: 6.92E-05mmHg at 25°C
• Melting Point: 216-218 °C
• Refractive Index: 1.569
• Boiling Point: 343.7±42.0 °C at 760 mmHg
• PKA: 3.53±0.40(Predicted)
• Flash Point: 161.7±27.9 °C
• PSA: 59.42000
• Density: 1.2±0.1 g/cm³
• LogP: 2.11710
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 217.07389321
• Heavy Atom Count: 16
• Complexity: 335

Purity/Quality:

99% ^*data from raw suppliers

Ethyl4-Hydroxyquinoline-2-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCOC(=O)C1=CC(=O)C2=CC=CC=C2N1

Technology Process of Ethyl 4-hydroxyquinoline-2-carboxylate

There total 10 articles about Ethyl 4-hydroxyquinoline-2-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:

ethyl 4-hydroxyquinoline-2-carboxylate (2401-97-0) → ethyl 4-hydroxyquinoline-2-carboxylate (24782-43-2)

Guidance literature:

With polyphosphoric acid; at 120 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.bmcl.2009.12.061

Reference yield:

aniline (62-53-3) + diethyl oxaloacetate (108-56-5) → ethyl 4-hydroxyquinoline-2-carboxylate (24782-43-2)

Guidance literature:

With benzene; Erhitzen des Reaktionsprodukts mit Diphenylaether;

DOI:10.1021/ja01216a080

Reference yield:

aniline (62-53-3) → ethyl 4-hydroxyquinoline-2-carboxylate (24782-43-2)

Guidance literature:

Multi-step reaction with 2 steps

1: toluene-4-sulfonic acid / cyclohexane / 48 h / Inert atmosphere; Reflux; Dean-Stark

2: polyphosphoric acid / 1 h / 120 °C / Inert atmosphere

With toluene-4-sulfonic acid; In cyclohexane;

DOI:10.1039/c3md00249g

upstream raw materials:

4-(2-nitrophenyl)-2,4-dioxobutanoic acid

aniline

diethyl oxaloacetate

2-acetylnitrobenzene

Downstream raw materials:

4-chloro-2-ethoxycarbonylquinoline

ethyl 4-bromo-quinoline-2-carboxylate

3-chloro-4-hydroxy-quinoline-2-carboxylic acid ethyl ester

4-hydroxy-3-iodo-quinoline-2-carboxylic acid ethyl ester

Refernces

• 1、 Sloan, Nikki L.,Luthra, Sajinder K.,McRobbie, Graeme,Pimlott, Sally L.,Sutherland, Andrew. "Late stage iodination of biologically active agents using a one-pot process from aryl amines". . p. 54881 - 54891. Retrieved 2017/12/12.
• 2、 Stevenson, Louise,Tavares, Adriana A.S.,Brunet, Aurelie,McGonagle, Fiona I.,Dewar, Deborah,Pimlott, Sally L.,Sutherland, Andrew. "New iodinated quinoline-2-carboxamides for SPECT imaging of the translocator protein". supporting information; experimental part. p. 954 - 957. Retrieved 2010/06/11.