4-Hydroxy-6-methoxyquinoline-3-carbonitrile

Base Information

• Chemical Name: 4-Hydroxy-6-methoxyquinoline-3-carbonitrile
• CAS No.: 13669-61-9
• Molecular Formula: C₁₁H₈N₂O₂
• Molecular Weight: 200.197
• Hs Code.: 2933499090
• NSC Number: 366401
• DSSTox Substance ID: DTXSID30320925
• Wikidata: Q72484968
• Mol file: 13669-61-9.mol

Synonyms:4-HYDROXY-6-METHOXYQUINOLINE-3-CARBONITRILE;13669-61-9;423180-88-5;6-methoxy-4-oxo-1H-quinoline-3-carbonitrile;6-Methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile;3-Quinolinecarbonitrile, 4-hydroxy-6-methoxy-;3-Quinolinecarbonitrile, 1,4-dihydro-6-methoxy-4-oxo-;NSC366401;4-Hydroxy-6-(methyloxy)-3-quinolinecarbonitrile;SCHEMBL3273442;DTXSID30320925;AMY32431;MFCD09743998;AKOS000182227;AKOS005198952;NSC 366401;NSC-366401;SB69638;AS-48027;FT-0687281;EN300-258624;F17565;A807112;3-Quinolinecarbonitrile,1,4-dihydro-6-methoxy-4-oxo-;6-methoxy-4-oxidanylidene-1H-quinoline-3-carbonitrile;6-methoxy-4-oxo-1,4-dihydro-quinoline-3-carbonitrile;Z2469606560

Chemical Property of 4-Hydroxy-6-methoxyquinoline-3-carbonitrile

Chemical Property:

• Vapor Pressure: 3.01E-05mmHg at 25°C
• Boiling Point: 356°Cat760mmHg
• PKA: 1.21±0.50(Predicted)
• Flash Point: 169.1°C
• PSA: 66.14000
• Density: 1.32g/cm³
• LogP: 1.82068
• XLogP3: 1.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 200.058577502
• Heavy Atom Count: 15
• Complexity: 353

Purity/Quality:

98% ^*data from raw suppliers

4-Hydroxy-6-methoxyquinoline-3-carbonitrile 95% ^*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#N

Technology Process of 4-Hydroxy-6-methoxyquinoline-3-carbonitrile

There total 8 articles about 4-Hydroxy-6-methoxyquinoline-3-carbonitrile 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: 85.0%

acetonitrile (75-05-8,26809-02-9) + (E)-methyl 2-(((dimethylamino)methylene)amino)-5-methoxybenzoate (872714-53-9) → 4-hydroxy-6-methoxyquinoline-3-carbonitrile (13669-61-9)

Guidance literature:

acetonitrile; With n-butyllithium; In tetrahydrofuran; at -72 ℃; for 1h;

(E)-methyl 2-(((dimethylamino)methylene)amino)-5-methoxybenzoate; In tetrahydrofuran; at -72 - 20 ℃;

With acetic acid; In tetrahydrofuran; for 1h;

Reference yield: 82.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + 3-(2-bromo-5-methoxyphenyl)-3-oxopropanenitrile → 6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile (423180-88-5,13669-61-9)

Guidance literature:

With ammonium hydroxide; potassium carbonate; L-proline; copper dichloride; for 22h; Reflux;

DOI:10.1002/adsc.201900286

Reference yield:

α-lithioacetonitrile (20428-58-4) + (E)-methyl 2-(((dimethylamino)methylene)amino)-5-methoxybenzoate (872714-53-9) → 6-methoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile (423180-88-5,13669-61-9)

Guidance literature:

α-lithioacetonitrile; (E)-methyl 2-(((dimethylamino)methylene)amino)-5-methoxybenzoate; In tetrahydrofuran; at -78 ℃;

With acetic acid; at 20 ℃;

DOI:10.1016/S0960-894X(00)00580-1

upstream raw materials:

acetonitrile

(E)-methyl 2-(((dimethylamino)methylene)amino)-5-methoxybenzoate

2-amino-5-hydroxybenzoic acid

α-lithioacetonitrile

Downstream raw materials:

4-chloro-6-methoxy-quinoline-3-carbonitrile

4-bromo-6-(methyloxy)-3-quinolinecarbonitrile

Refernces

• 1、 Gore, Babasaheb Sopan,Lee, Chein Chung,Lee, Jessica,Wang, Jeh-Jeng. "Copper-Catalyzed Synthesis of Substituted 4-Quinolones using Water as a Benign Reaction Media: Application for the Construction of Oxolinic Acid and BQCA". supporting information. . Retrieved 2019/05/24.
• 2、 -. "ANTIBACTERIAL AGENTS". Page/Page column 62. . Retrieved 2010/02/15.