4-HYDROXY-6-METHOXYQUINOLINE

Base Information

• Chemical Name: 4-HYDROXY-6-METHOXYQUINOLINE
• CAS No.: 13788-72-2
• Molecular Formula: C10H9NO2
• Molecular Weight: 175.184
• Mol file: 13788-72-2.mol

Synonyms:4(1H)-Quinolone,6-methoxy- (8CI);6-Methoxy-4-quinolone;NSC 266150;

Chemical Property of 4-HYDROXY-6-METHOXYQUINOLINE

Chemical Property:

• Melting Point: 251-252 °C
• Boiling Point: 321.5 °C at 760 mmHg
• PKA: 3.07±0.50(Predicted)
• Flash Point: 148.2 °C
• Density: 1.199g/cm³

Purity/Quality:

98%min ^*data from raw suppliers

6-Methoxyquinolin-4(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-HYDROXY-6-METHOXYQUINOLINE

There total 20 articles about 4-HYDROXY-6-METHOXYQUINOLINE 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: 88.0%

6-methoxy-2,3-dihydroquinolin-4(1H)-one (3835-21-0) → 6-methoxy-4(1H)-quinolinone (13788-72-2)

Guidance literature:

With palladium 10% on activated carbon; sodium hydroxide; In water; isopropyl alcohol; for 16h; Inert atmosphere; Reflux;

DOI:10.1071/CH10465

Reference yield: 76.0%

Methyl formate (107-31-3) + 1-(2-amino-5-methoxy-phenyl)-ethanone (23042-77-5) → 6-methoxy-4(1H)-quinolinone (13788-72-2)

Guidance literature:

With sodium hydride; at 40 ℃; for 24h; Inert atmosphere; Schlenk technique;

DOI:10.1002/chem.201405852

Reference yield: 71.0%

2,2-dimethyl-5-(((4-methoxyphenyl)amino)methylene)-1,3-dioxane-4,6-dione (25063-43-8) → 6-methoxy-4(1H)-quinolinone (13788-72-2)

Guidance literature:

In diphenylether; for 0.25h; Heating;

upstream raw materials:

2,2-dimethyl-5-(((4-methoxyphenyl)amino)methylene)-1,3-dioxane-4,6-dione

malonic acid

4-methoxy-aniline

orthoformic acid triethyl ester

Downstream raw materials:

1-benzyloxycarbonyl-6-methoxy-4-quinolone

4-bromo-6-methoxyquinoline

Refernces

• 1、 Wang, Fen,Jin, Liang,Kong, Lingheng,Li, Xingwei. "Cobalt(III)- and Rhodium(III)-Catalyzed C-H Amidation and Synthesis of 4-Quinolones: C-H Activation Assisted by Weakly Coordinating and Functionalizable Enaminone". . p. 1812 - 1815. Retrieved 2017.
• 2、 Huang, Xian,Liu, Zhanxiang. "Preparation of a resin-bound cyclic malonic ester and a facile solid-phase synthesis of 4(1H)quinolones". . p. 7655 - 7657. Retrieved 2001.
• 3、 Maestro, Aitor,Lemaire, Sebastien,Harutyunyan, Syuzanna R.. "Cu(I)-Catalyzed Alkynylation of Quinolones". supporting information. p. 1228 - 1231. Retrieved 2022/02/14.