4-Hydroxy-8-methoxy-2-methylquinoline

Base Information

• Chemical Name: 4-Hydroxy-8-methoxy-2-methylquinoline
• CAS No.: 15644-89-0
• Molecular Formula: C11H11NO2
• Molecular Weight: 189.214
• Hs Code.: 2933499090
• European Community (EC) Number: 803-142-9
• NSC Number: 208722
• DSSTox Substance ID: DTXSID70935451
• Wikidata: Q72484847
• Mol file: 15644-89-0.mol

Synonyms:15644-89-0;4-Hydroxy-8-methoxy-2-methylquinoline;8-methoxy-2-methylquinolin-4-ol;8-Methoxy-2-methylquinolin-4(1H)-one;8-methoxy-2-methyl-1H-quinolin-4-one;50553-62-3;8-Methoxy-2-methyl-quinolin-4-ol;NSC208722;Oprea1_201217;Oprea1_263649;SCHEMBL1564292;O(C)c1cccc2c(O)cc(C)nc12;SCHEMBL20605619;DTXSID70935451;HMS1675K10;8-Methoxy-2-methyl-4-quinolinol #;MFCD00272321;STK523661;AKOS000507494;Quinolin-4-ol, 8-methoxy-2-methyl-;AB05592;NSC-208722;SB67868;AS-53715;CS-0227024;EU-0018456;FT-0618677;EN300-110909;P16937;A809749;SR-01000521875;4-Hydroxy-8-methoxy-2-methylquinoline, AldrichCPR;SR-01000521875-1;F0907-0835

Chemical Property of 4-Hydroxy-8-methoxy-2-methylquinoline

Chemical Property:

• Vapor Pressure: 0.000239mmHg at 25°C
• Refractive Index: 1.557
• Boiling Point: 352.634 °C at 760 mmHg
• Flash Point: 167.067 °C
• PSA: 42.35000
• Density: 1.217 g/cm³
• LogP: 2.25740
• Storage Temp.: 2-8°C
• XLogP3: 1.9
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 189.078978594
• Heavy Atom Count: 14
• Complexity: 273

Purity/Quality:

98%min ^*data from raw suppliers

8-methoxy-2-methylquinolin-4-ol ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1=CC(=O)C2=C(N1)C(=CC=C2)OC

Technology Process of 4-Hydroxy-8-methoxy-2-methylquinoline

There total 7 articles about 4-Hydroxy-8-methoxy-2-methylquinoline 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: 97.0%

ethyl acetoacetate (141-97-9) + 2-methoxy-phenylamine (90-04-0) → 8-methoxy-2-methyl-4-quinolinol (15644-89-0)

Guidance literature:

With polyphosphoric acid; at 120 ℃;

DOI:10.1016/j.bioorg.2021.105008

Reference yield: 48.7%

ethyl 3-<(2-methoxyphenyl)amino>but-2-enoate (33267-45-7) → 8-methoxy-2-methyl-4-quinolinol (15644-89-0)

Guidance literature:

In diphenylether; at 235 ℃; for 3h;

DOI:10.1021/jm030159x

Reference yield: 37.0%

ethyl (E)-3-((2-methoxyphenyl)amino)but-2-enoate → 8-methoxy-2-methyl-4-quinolinol (15644-89-0)

Guidance literature:

In diethyl ether; at 235 ℃; for 1h;

DOI:10.1016/j.ejmech.2020.112948

upstream raw materials:

ethyl (Z)-3-((2-methoxyphenyl)amino)but-2-enoate

ethyl acetoacetate

2-methoxy-phenylamine

ethyl 3-<(2-methoxyphenyl)amino>but-2-enoate

Downstream raw materials:

2-methoxy-6-(3-methyl-1H-pyrazol-5-yl)aniline

4-bromo-8-methoxy-2-methylquinoline

Refernces

• 1、 Li, Baicun,Yao, Jie,Guo, Kaiqiang,He, Fengming,Chen, Kun,Lin, Zongxin,Liu, Shunzhi,Huang, Jiangang,Wu, Qiaoqiong,Fang, Meijuan,Zeng, Jinzhang,Wu, Zhen. "Design, synthesis, and biological evaluation of 5-((8-methoxy-2-methylquinolin-4-yl)amino)-1H-indole-2-carbohydrazide derivatives as novel Nur77 modulators". . . Retrieved 2020.
• 2、 Chang, Feng-Shuo,Chen, Weichung,Wang, Chihuei,Tzeng, Cherng-Chyi,Chen, Yeh-Long. "Synthesis and antiproliferative evaluations of certain 2-phenylvinylquinoline (2-styrylquinoline) and 2-furanylvinylquinoline derivatives". experimental part. p. 124 - 133. Retrieved 2010/04/06.