4-Hydroxy-5,7-dimethoxyquinoline-3-carbonitrile

Base Information

• Chemical Name: 4-Hydroxy-5,7-dimethoxyquinoline-3-carbonitrile
• CAS No.: 331662-65-8
• Molecular Formula: C₁₂H₁₀N₂O₃
• Molecular Weight: 230.223
• Hs Code.: 2933499090
• DSSTox Substance ID: DTXSID80444761
• Wikidata: Q82263011
• Mol file: 331662-65-8.mol

Synonyms:331662-65-8;4-hydroxy-5,7-dimethoxyquinoline-3-carbonitrile;5,7-dimethoxy-4-oxo-1H-quinoline-3-carbonitrile;5,7-dimethoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile;4-hydroxy-5,7-dimethoxy-3-quinolinecarbonitrile;3-Quinolinecarbonitrile, 1,4-dihydro-5,7-dimethoxy-4-oxo-;SCHEMBL5459454;DTXSID80444761;STL434921;AKOS000194863;AKOS005185209;SB70859;EN300-71492;Z234897477

Chemical Property of 4-Hydroxy-5,7-dimethoxyquinoline-3-carbonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 407.026°C at 760 mmHg
• Flash Point: 199.962°C
• PSA: 75.11000
• Density: 1.332g/cm³
• LogP: 1.41698
• XLogP3: 1.4
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 2
• Exact Mass: 230.06914219
• Heavy Atom Count: 17
• Complexity: 396

Purity/Quality:

98.5% ^*data from raw suppliers

5,7-Dimethoxy-4-oxo-1,4-dihydroquinoline-3-carbonitrile ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: COC1=CC2=C(C(=C1)OC)C(=O)C(=CN2)C#N

Technology Process of 4-Hydroxy-5,7-dimethoxyquinoline-3-carbonitrile

There total 4 articles about 4-Hydroxy-5,7-dimethoxyquinoline-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: 88.0%

ethyl 2-cyano-3-(3,5-dimethoxyphenylamino)acrylate (712307-63-6) → 5,7-dimethoxy-4-hydroxy-3-quinolinecarbonitrile (331662-65-8)

Guidance literature:

In diphenylether; for 72h; Heating;

DOI:10.1021/jm000420z

Reference yield:

α-lithioacetonitrile (20428-58-4) + 2-(dimethylamino-methyleneamino)-4,6-dimethoxy-benzoic acid methyl ester → 5,7-dimethoxy-4-hydroxy-3-quinolinecarbonitrile (331662-65-8)

Guidance literature:

α-lithioacetonitrile; 2-(dimethylamino-methyleneamino)-4,6-dimethoxy-benzoic acid methyl ester; In tetrahydrofuran; at -78 ℃;

With acetic acid; at 20 ℃;

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

Reference yield:

3.5-dimethoxyaniline (10272-07-8) → 5,7-dimethoxy-4-hydroxy-3-quinolinecarbonitrile (331662-65-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / 0.75 h / 120 °C

2: 88 percent / diphenyl ether; various solvent(s) / 72 h / Heating

In diphenylether;

DOI:10.1021/jm000420z

upstream raw materials:

α-lithioacetonitrile

ethyl 2-cyano-3-(3,5-dimethoxyphenylamino)acrylate

3.5-dimethoxyaniline

methyl 2-amino-4,6-dimethoxybenzoate

Downstream raw materials:

4-chloro-5,7-dimethoxy-3-quinolinecarbonitrile