6-Methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Base Information

• Chemical Name: 6-Methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile
• CAS No.: 123990-79-4
• Molecular Formula: C₁₁H₈N₂O₂
• Molecular Weight: 200.197
• Hs Code.: 2933790090
• European Community (EC) Number: 835-357-9
• DSSTox Substance ID: DTXSID20561108
• Wikidata: Q82444770
• Mol file: 123990-79-4.mol

Synonyms:123990-79-4;6-Methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile;6-methoxy-2-oxo-1H-quinoline-3-carbonitrile;6-METHOXY-2-OXO-1,2-DIHYDRO-QUINOLINE-3-CARBONITRILE;2-HYDROXY-6-METHOXYQUINOLINE-3-CARBONITRILE;3-Quinolinecarbonitrile,1,2-dihydro-6-methoxy-2-oxo-;SCHEMBL7499153;DTXSID20561108;MFCD02588850;AKOS004121577;AKOS006221630;AT26840;NS-02035;EN300-734676

Chemical Property of 6-Methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

Chemical Property:

• Boiling Point: 458.839 °C at 760 mmHg
• Flash Point: 231.298 °C
• PSA: 65.88000
• Density: 1.365 g/cm³
• LogP: 1.40838
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 200.058577502
• Heavy Atom Count: 15
• Complexity: 353

Purity/Quality:

99% ^*data from raw suppliers

6-Methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile ^*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(=O)C(=C2)C#N

Technology Process of 6-Methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

There total 5 articles about 6-Methoxy-2-oxo-1,2-dihydroquinoline-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: 80.0%

2-chloro-6-methoxyquinoline-3-carbonitrile (101617-91-8) → 6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (123990-79-4)

Guidance literature:

With hydrogenchloride; In methanol;

Reference yield: 75.0%

C11H11BrN2O2 → 6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (123990-79-4)

Guidance literature:

With copper(l) iodide; potassium carbonate; L-proline; In ethylene glycol; at 110 ℃; for 10h;

DOI:10.1002/ejoc.201301373

Reference yield:

2-bromo-5-methoxybenzyl bromide (19614-12-1) → 6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile (123990-79-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0.08 h / 90 °C

1.2: 2 h / 90 °C

2.1: copper(l) iodide; L-proline; potassium carbonate / ethylene glycol / 10 h / 110 °C

With copper(l) iodide; potassium carbonate; L-proline; In ethylene glycol; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.201301373

upstream raw materials:

2-amino-5-methoxybenzaldehyde

ethyl 2-cyanoacetate

5-methoxy-2-nitro-benzaldehyde

2-chloro-6-methoxyquinoline-3-carbonitrile