Ethyl 2-cyano-1(2H)-quinolinecarboxylate

Base Information

• Chemical Name: Ethyl 2-cyano-1(2H)-quinolinecarboxylate
• CAS No.: 17954-23-3
• Molecular Formula: C13H12 N2 O2
• Molecular Weight: 228.25
• Hs Code.: 2933499090
• NSC Number: 131480
• DSSTox Substance ID: DTXSID30299581
• Nikkaji Number: J104.718C
• Mol file: 17954-23-3.mol

Synonyms:ethyl 2-cyano-2H-quinoline-1-carboxylate;17954-23-3;Ethyl 2-cyano-1(2H)-quinolinecarboxylate;1,2-Dihydro-2-cyanoquinoline-1-carboxylic acid ethyl ester;NSC131480;1(2H)-Quinolinecarboxylic acid, 2-cyano-, ethyl ester;DTXSID30299581;QFAHEDSFVHOFGW-UHFFFAOYSA-N;NSC-131480;Ethyl 2-cyano-1(2H)-quinolinecarboxylate #;Ethyl 2-cyano-1,2-dihydroquinolinecarboxylate

Chemical Property of Ethyl 2-cyano-1(2H)-quinolinecarboxylate

Chemical Property:

• Vapor Pressure: 1.79E-06mmHg at 25°C
• Boiling Point: 395.8°Cat760mmHg
• Flash Point: 193.2°C
• PSA: 53.33000
• Density: 1.24g/cm³
• LogP: 2.63348
• XLogP3: 2.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 228.089877630
• Heavy Atom Count: 17
• Complexity: 369

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)N1C(C=CC2=CC=CC=C21)C#N

Technology Process of Ethyl 2-cyano-1(2H)-quinolinecarboxylate

There total 5 articles about Ethyl 2-cyano-1(2H)-quinolinecarboxylate 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%

quinoline (91-22-5) + potassium cyanide + chloroformic acid ethyl ester (541-41-3) → 1-ethoxycarbonyl-1,2-dihydroquinoline-2-carbonitrile (17954-23-3)

Guidance literature:

In dichloromethane; water; at 20 ℃; for 2h;

DOI:10.5012/bkcs.2010.31.10.3031

Reference yield:

trimethylsilyl cyanide (7677-24-9) + 1-(ethoxycarbonyl)quinolinium chloride (82700-07-0) → 1-ethoxycarbonyl-1,2-dihydroquinoline-2-carbonitrile (17954-23-3)

Guidance literature:

With iodine; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tetlet.2005.03.127

Reference yield:

quinoline (91-22-5) → 1-ethoxycarbonyl-1,2-dihydroquinoline-2-carbonitrile (17954-23-3)

Guidance literature:

Multi-step reaction with 2 steps

1: CH₂Cl₂ / 0.5 h / 20 °C

2: iodine / CH₂Cl₂ / 3 h / 20 °C

With iodine; In dichloromethane;

DOI:10.1016/j.tetlet.2005.03.127

upstream raw materials:

quinoline

chloroformic acid ethyl ester

trimethylsilyl cyanide

1-(ethoxycarbonyl)quinolinium chloride

Downstream raw materials:

1-oxo-3-phenyl-oxazolo[3,4-a]quinoline-3a-carbonitrile

3-phenyl-oxazolo[3,4-a]quinolin-1-one

1-Benzyl-5H-pyrido[4,3-b]indol-3-ylamine; compound with acetic acid

1-Phenyl-5H-pyrido[4,3-b]indol-3-ylamine; compound with acetic acid

Refernces

• 1、 Yadav,Reddy,Srinivas,Sathaiah. "Allylation and cyanation of aza-aromatics activated by chloroformate and a catalytic amount of iodine". . p. 3489 - 3492. Retrieved 2007/10/03.