4-Hydroxy-6-methoxyquinoline-3-carboxylic acid

Base Information

• Chemical Name: 4-Hydroxy-6-methoxyquinoline-3-carboxylic acid
• CAS No.: 28027-16-9
• Molecular Formula: C₁₁H₉NO₄
• Molecular Weight: 219.197
• Hs Code.: 2933499090
• European Community (EC) Number: 862-890-4
• NSC Number: 80675
• DSSTox Substance ID: DTXSID80292183
• Wikidata: Q72484972
• ChEMBL ID: CHEMBL386037
• Mol file: 28027-16-9.mol

Synonyms:4-HYDROXY-6-METHOXYQUINOLINE-3-CARBOXYLIC ACID;28027-16-9;34785-07-4;6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylic acid;3-Carboxy-4-hydroxy-6-methoxyquinoline;4-Hydroxy-6-methoxy-quinoline-3-carboxylic acid;6-methoxy-4-oxo-1H-quinoline-3-carboxylic acid;6-Methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid;MFCD00024003;MFCD00844091;NSC80675;Oprea1_207356;Oprea1_511176;4-HYDROXY-6-METHOXY-3-QUINOLINECARBOXYLIC ACID;CHEMBL386037;SCHEMBL2053494;DTXSID80292183;YUXLPEGMXYHPCZ-UHFFFAOYSA-N;HMS1609L06;AMY27556;BBL027898;NSC-80675;STK802004;STK954972;AKOS000559094;AKOS001523843;AB01402;CCG-105912;CS-W010476;SB71633;AC-24335;DS-11062;BB 0221659;EU-0004226;FT-0638746;FT-0657994;VU0056123-3;VU0612445-1;EN300-398543;F15002;AB00100274-01;4-Hydroxy-6-methoxy-quinoline-3-carboxylic acid;A819290;A822396;J-515503;J-518849;J-650160;6-methoxy-4-oxo-1,4-dihydroquinoline-3-carboxylicacid;F3095-2073;F3367-0003;Z431512324;6-Methoxy-4-oxo-1,4-dihydro-3-quinolinecarboxylic acid, AldrichCPR;290821-27-1

Chemical Property of 4-Hydroxy-6-methoxyquinoline-3-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.71E-07mmHg at 25°C
• Melting Point: 278-279 °C (decomp)
• Boiling Point: 411°Cat760mmHg
• PKA: 0.74±0.30(Predicted)
• Flash Point: 202.4°C
• PSA: 79.65000
• Density: 1.402g/cm³
• LogP: 1.64720
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 219.05315777
• Heavy Atom Count: 16
• Complexity: 350

Purity/Quality:

97% ^*data from raw suppliers

4-Hydroxy-6-methoxyquinoline-3-carboxylicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC2=C(C=C1)NC=C(C2=O)C(=O)O

Technology Process of 4-Hydroxy-6-methoxyquinoline-3-carboxylic acid

There total 3 articles about 4-Hydroxy-6-methoxyquinoline-3-carboxylic acid 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: 99.0%

ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate (77156-78-6) → 4-hydroxy-6-methoxy-3-quinoline carboxylic acid (28027-16-9)

Guidance literature:

With sodium hydroxide; In water; at 90 ℃; for 1.5h;

DOI:10.1016/j.tetlet.2017.01.042

Reference yield:

diethyl 2-(((4-methoxyphenyl)amino)methylene)malonate (83507-70-4) → 4-hydroxy-6-methoxy-3-quinoline carboxylic acid (28027-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyl ether biphenyl mixture

2: aqueous HCl

With hydrogenchloride; diphenylether; biphenyl;

DOI:10.1021/ja01211a020

Reference yield:

4-methoxy-aniline (104-94-9) → 4-hydroxy-6-methoxy-3-quinoline carboxylic acid (28027-16-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: toluene / 1 h / Heating

1.2: 36 percent / diphenyl ether / 1 h / Heating

2.1: aq. sodium hydroxide / 1 h / Heating

With sodium hydroxide; In toluene;

DOI:10.1248/cpb.55.821

upstream raw materials:

ethyl 4-hydroxy-6-methoxyquinoline-3-carboxylate

4-methoxy-aniline

diethyl 2-(((4-methoxyphenyl)amino)methylene)malonate

Downstream raw materials:

4-hydroxy-6-methoxyquinoline

4-chloro-quinolin-6-ol