6-hydroxy-4-methyl-1H-quinolin-2-one

Base Information

• Chemical Name: 6-hydroxy-4-methyl-1H-quinolin-2-one
• CAS No.: 34982-01-9
• Molecular Formula: C10H9 N O2
• Molecular Weight: 175.18
• Hs Code.: 2933790090
• Mol file: 34982-01-9.mol

Synonyms:Carbostyril,6-hydroxy-4-methyl- (8CI); 2,6-Dihydroxy-4-methylquinoline;4-Methyl-2,6-quinolinediol; 6-Hydroxy-4-methylcarbostyril;6-Hydroxy-4-methylquinolin-2(1H)-one

Chemical Property of 6-hydroxy-4-methyl-1H-quinolin-2-one

Chemical Property:

• Vapor Pressure: 2.96E-08mmHg at 25°C
• Boiling Point: 437.2°Cat760mmHg
• Flash Point: 218.2°C
• PSA: 53.35000
• Density: 1.264g/cm³
• LogP: 1.95440

Purity/Quality:

98%Min ^*data from raw suppliers

4-Methylquinoline-2,6-diol ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xi,Xn
• Statements: 22-41
• Safety Statements: 26-39

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-hydroxy-4-methyl-1H-quinolin-2-one

There total 8 articles about 6-hydroxy-4-methyl-1H-quinolin-2-one 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%

6-methoxy-4-methyl-2-oxo-1H-quinoline (5342-23-4) → 4-methyl-6-hydroxy-2-oxo-1,2-dihydroquinoline (34982-01-9)

Guidance literature:

With hydrogen bromide; acetic acid; for 75h; Reflux;

DOI:10.1016/j.bmc.2010.04.011

Reference yield: 76.0%

Ethyl 2-butynoate (4341-76-8) + 4-acetaminophenol (103-90-2,8055-08-1) → 4-methyl-6-hydroxy-2-oxo-1,2-dihydroquinoline (34982-01-9)

Guidance literature:

With silver hexafluoroantimonate; [RhCl₂(p-cymene)]2; trimethylpyruvic acid; In isopropyl alcohol; at 130 ℃; for 24h; Inert atmosphere; Glovebox;

DOI:10.1021/ol501548e

Reference yield:

4'-methoxyacetoacetanilide (5437-98-9) → 4-methyl-6-hydroxy-2-oxo-1,2-dihydroquinoline (34982-01-9) + 6-methoxy-4-methyl-2-oxo-1H-quinoline (5342-23-4)

Guidance literature:

With sulfuric acid; at 95 ℃;

DOI:10.1016/j.cclet.2016.01.029

upstream raw materials:

6-methoxy-4-methyl-2-oxo-1H-quinoline

acetoacetic acid-(4-hydroxy-anilide)

Ethyl 2-butynoate

4-acetaminophenol

Downstream raw materials:

2,6-dihydroxy-quinoline-4-carboxylic acid

4-[(2-chloro-6-hydroxy-4-methylquinolin-5-yl)methyl]-5-(4-methylphenyl)-2,3-dihydro-1H-pyrazol-3-one

8-chloro-10-methyl-2-(4-methylbenzoyl)-3H-chromeno[6,5-b]pyridin-3-one

methyl 3-[(4-methyl-2-oxo-1,2-dihydro-6-quinolinyl)oxy]methylbenzoate

Refernces

• 1、 Pan, Le,Li, Xiu-Zhuang,Sun, Di-An,Jin, Hui,Guo, Hong-Ru,Qin, Bo. "Design and synthesis of novel coumarin analogs and their nematicidal activity against five phytonematodes". . p. 375 - 379. Retrieved 2016.
• 2、 Manikandan, Rajendran,Jeganmohan, Masilamani. "Ruthenium-catalyzed cyclization of anilides with substituted propiolates or acrylates: An efficient route to 2-quinolinones". supporting information. p. 3568 - 3571. Retrieved 2014/07/21.