6-Methoxy-2-methyl-8-nitroquinoline

Base Information

• Chemical Name: 6-Methoxy-2-methyl-8-nitroquinoline
• CAS No.: 54232-06-3
• Molecular Formula: C11H10N2O3
• Molecular Weight: 218.2087
• European Community (EC) Number: 660-982-7
• NSC Number: 75683
• DSSTox Substance ID: DTXSID40291455
• Nikkaji Number: J1.474.274C
• Wikidata: Q82029417
• Mol file: 54232-06-3.mol

Synonyms:6-Methoxy-2-methyl-8-nitroquinoline;54232-06-3;2-Methyl-6-methoxy-8-nitroquinoline;Quinoline, 6-methoxy-2-methyl-8-nitro-;NSC75683;SCHEMBL10622390;DTXSID40291455;NSC 75683;NSC-75683;AKOS022889321;6-Methoxy-2-methyl-8-nitroquinoline #

Chemical Property of 6-Methoxy-2-methyl-8-nitroquinoline

Chemical Property:

• Vapor Pressure: 1.98E-05mmHg at 25°C
• Refractive Index: 1.631
• Boiling Point: 373 °C at 760 mmHg
• Flash Point: 179.4 °C
• Density: 1.292 g/cm³
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 1
• Exact Mass: 218.06914219
• Heavy Atom Count: 16
• Complexity: 266

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=NC2=C(C=C(C=C2C=C1)OC)[N+](=O)[O-]

Technology Process of 6-Methoxy-2-methyl-8-nitroquinoline

There total 4 articles about 6-Methoxy-2-methyl-8-nitroquinoline 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: 77.0%

4-methoxy-2-nitroaniline (96-96-8) + crotonaldehyde (123-73-9,4170-30-3) → 6-methoxy-2-methyl-8-nitroquinoline (54232-06-3)

Guidance literature:

4-methoxy-2-nitroaniline; With hydrogenchloride; In water; for 0.25h; Reflux;

crotonaldehyde; In water; for 1h; Reflux;

DOI:10.1002/ejic.201901323

Reference yield: 41.0%

acetaldehyde (75-07-0,9002-91-9) + 4-methoxy-2-nitroaniline (96-96-8) → 6-methoxy-2-methyl-8-nitroquinoline (54232-06-3)

Guidance literature:

With hydrogenchloride; In water; at 0 - 80 ℃; for 1.25h;

DOI:10.1016/j.crci.2019.05.003

Reference yield: 18.0%

paracetaldehyde (123-63-7) + 4-methoxy-2-nitroaniline (96-96-8) → 6-methoxy-2-methyl-8-nitroquinoline (54232-06-3)

Guidance literature:

With hydrogenchloride; Heating;

DOI:10.1016/j.bmc.2004.01.021

upstream raw materials:

paracetaldehyde

4-methoxy-2-nitroaniline

crotonaldehyde

acetaldehyde

Downstream raw materials:

6-methoxy-8-nitro-2-[(E)-2-phenyl-1-ethenyl]quinoline

5,8-Dinitro-6-methoxy-2-methylchinolin

7-Brom-6-methoxy-2-methyl-5,8-chinolindion

8-amino-6-methoxy-2-[(E)-2-phenyl-1-ethenyl]quinoline

Refernces

• 1、 Huang, Ju,Nguyen, Michel,Liu, Yan,Robert, Anne,Meunier, Bernard. "Synthesis and characterization of 8-aminoquinolines, substituted by electron donating groups, as high-affinity copper chelators for the treatment of Alzheimer's disease". . p. 419 - 427. Retrieved 2019/06/13.
• 2、 Liao,Nyberg,Cheng. "Synthetic studies of the antitumor antibiotic streptonigrin. I. Synthesis of the A B ring portion of streptonigrin". . p. 1063 - 1065. Retrieved 2007/10/08.