METHYL 8-NITRO-4-OXO-1,4-DIHYDROQUINOLINE-2-CARBOXYLATE

Base Information

• Chemical Name: METHYL 8-NITRO-4-OXO-1,4-DIHYDROQUINOLINE-2-CARBOXYLATE
• CAS No.: 16134-01-3
• Molecular Formula: C11H8 N2 O5
• Molecular Weight: 248.195
• Hs Code.: 2933499090
• Mol file: 16134-01-3.mol

Synonyms:Quinaldicacid, 1,4-dihydro-8-nitro-4-oxo-, methyl ester (8CI)

Chemical Property of METHYL 8-NITRO-4-OXO-1,4-DIHYDROQUINOLINE-2-CARBOXYLATE

Chemical Property:

• Melting Point: 198-199 °C(Solv: dimethyl sulfoxide (67-68-5); water (7732-18-5))
• Boiling Point: 405.3±45.0 °C(Predicted)
• PKA: -4.01±0.70(Predicted)
• PSA: 104.98000
• Density: 1.463±0.06 g/cm3(Predicted)
• LogP: 1.74610

Purity/Quality:

98%min ^*data from raw suppliers

8-Nitro-4-oxo-1,4-dihydro-quinoline-2-carboxylicacidmethylester ＞97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of METHYL 8-NITRO-4-OXO-1,4-DIHYDROQUINOLINE-2-CARBOXYLATE

There total 14 articles about METHYL 8-NITRO-4-OXO-1,4-DIHYDROQUINOLINE-2-CARBOXYLATE 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: 84.0%

2-<(2-nitrophenyl)amino>-2-butenedioic acid dimethyl ester (17454-33-0) → methyl 1,4-dihydro-8-nitro-4-oxoquinoline-2-carboxylate (16134-01-3)

Guidance literature:

With polyphosphoric acid; at 180 ℃; for 0.75h; Inert atmosphere;

DOI:10.1016/j.tet.2012.05.001

Reference yield: 72.0%

2-<(2-nitrophenyl)amino>-2-butenedioic acid dimethyl ester (17454-33-0) → methyl 4-hydroxy-8-nitro-quinoline-2-carboxylate (495406-97-8,16134-01-3)

Guidance literature:

In diphenylether; at 250 ℃; for 0.25h; Reflux;

DOI:10.1021/jacs.0c12128

Reference yield: 65.0%

dimethyl 2-(2-nitrophenylamino)maleate (16133-96-3) → methyl 1,4-dihydro-8-nitro-4-oxoquinoline-2-carboxylate (16134-01-3)

Guidance literature:

With PPA; at 120 ℃;

DOI:10.1016/j.tet.2003.08.058

upstream raw materials:

2-<(2-nitrophenyl)amino>-2-butenedioic acid dimethyl ester

dimethyl 2-(2-nitrophenylamino)maleate

2-nitro-aniline

dimethyl acetylenedicarboxylate

Downstream raw materials:

C₁₈H₁₄N₂O₃

C₁₇H₁₂N₂O₃

C₁₇H₁₁ClN₂O₂

8-benzamido-N-(5-(5-(3-(dimethylamino)propylcarbamoyl)-1-methyl-1H-pyrrol-3-ylcarbamoyl)-1-methyl-1H-pyrrol-3-yl)quinoline-2-carboxamide

Refernces

• 1、 Li, Baolin,Pang, Zhi,Qi, Ting. "Assembly and optical properties of 1D helical bundles induced by triphenylamine, side chains and solvents in crystals". supporting information. p. 5555 - 5562. Retrieved 2021/07/02.
• 2、 Deora, Girdhar Singh,Kantham, Srinivas,Chan, Stephen,Dighe, Satish N.,Veliyath, Suresh K.,McColl, Gawain,Parat, Marie-Odile,McGeary, Ross P.,Ross, Benjamin P.. "Multifunctional Analogs of Kynurenic Acid for the Treatment of Alzheimer's Disease: Synthesis, Pharmacology, and Molecular Modeling Studies". . p. 2667 - 2675. Retrieved 2017/12/26.