7-Ethoxy-4-hydroxy-6-nitroquinoline-3-carbonitrile

Base Information

• Chemical Name: 7-Ethoxy-4-hydroxy-6-nitroquinoline-3-carbonitrile
• CAS No.: 214476-08-1
• Molecular Formula: C₁₂H₉N₃O₄
• Molecular Weight: 259.221
• DSSTox Substance ID: DTXSID60432303
• Wikidata: Q82246375
• Mol file: 214476-08-1.mol

Synonyms:214476-08-1;7-ETHOXY-4-HYDROXY-6-NITROQUINOLINE-3-CARBONITRILE;3-Cyano-7-ethoxy-4-hydroxy-6-nitroquinoline;7-ethoxy-6-nitro-4-oxo-1H-quinoline-3-carbonitrile;3-Quinolinecarbonitrile, 7-ethoxy-4-hydroxy-6-nitro-;MFCD13181132;7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile;3-Quinolinecarbonitrile,7-ethoxy-4-hydroxy-6-nitro-;SCHEMBL1894668;DTXSID60432303;YWXULSPHZDNVAN-UHFFFAOYSA-N;CS-B0222;AKOS027337495;SB71222;CS-11165;SY007478;FT-0665281;F13569;7-Ethoxy-6-nitro-4-oxo-1,4-dihydroquinoline-3-carbonitrile

Chemical Property of 7-Ethoxy-4-hydroxy-6-nitroquinoline-3-carbonitrile

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Boiling Point: 456.346oC at 760 mmHg
• PKA: -0.45±0.50(Predicted)
• Flash Point: 229.79oC
• PSA: 111.70000
• Density: 1.452g/cm3
• LogP: 2.22988
• Solubility.: DMSO
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 2
• Exact Mass: 259.05930578
• Heavy Atom Count: 19
• Complexity: 473

Purity/Quality:

≥95% ^*data from raw suppliers

3-Cyano-7-ethoxy-4-hydroxy-6-nitroquinoline ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC1=C(C=C2C(=C1)NC=C(C2=O)C#N)[N+](=O)[O-]
• Uses: Reagent used in the preparation of tyrosine kinase inhibiting antitumor agents. 3-Cyano-7-ethoxy-4-hydroxy-6-nitroquinoline is used in the preparation of tyrosine kinase inhibiting antitumor agents.

Technology Process of 7-Ethoxy-4-hydroxy-6-nitroquinoline-3-carbonitrile

There total 14 articles about 7-Ethoxy-4-hydroxy-6-nitroquinoline-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: 76.0%

(E)-2-Cyano-3-(3-ethoxy-4-nitro-phenylamino)-acrylic acid ethyl ester (492456-51-6) → 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile (214476-08-1)

Guidance literature:

With diphenyl ether-biphenyl eutectic; at 256 ℃; for 1.25h;

DOI:10.1021/jm020241c

Reference yield: 70.0%

(Z)-2-cyano-3-(5'-ethoxy-2'-methoxycarbonyl-4'-nitrophenyl)amino-2-propenoic acid t-butyl ester → 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile (214476-08-1)

Guidance literature:

With trifluorormethanesulfonic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; Heating / reflux;

Reference yield: 62.0%

7-ethoxy-4-hydroxyquinoline-3-carbonitrile (214476-07-0) → 7-Ethoxy-4-hydroxy-6-nitro-quinoline-3-carbonitrile (214476-08-1)

Guidance literature:

With ammonium nitrite; trifluoroacetic anhydride;

DOI:10.1021/jm020241c

upstream raw materials:

7-ethoxy-4-hydroxyquinoline-3-carbonitrile

(E)-2-Cyano-3-(3-ethoxy-4-nitro-phenylamino)-acrylic acid ethyl ester

5-methoxy-2-methyl-4-nitroaniline

3-(ethyloxy)-4-nitroaniline

Downstream raw materials:

4-Chloro-7-ethoxy-6-nitro-quinoline-3-carbonitrile

6-amino-4-(3-bromo-phenylamino)-7-ethoxy-quinoline-3-carbonitrile

4-(3-Bromo-phenylamino)-7-ethoxy-6-nitro-quinoline-3-carbonitrile

6-amino-4-(3-chloro-4-fluoro-phenylamino)-7-ethoxy-quinoline-3-carbonitrile