3-ACETYL-4-HYDROXY-1-METHYL-2(1H)-QUINOLINONE

Base Information

• Chemical Name: 3-ACETYL-4-HYDROXY-1-METHYL-2(1H)-QUINOLINONE
• CAS No.: 54289-76-8
• Molecular Formula: C12H11NO3
• Molecular Weight: 217.224
• Hs Code.: 2933499090
• Mol file: 54289-76-8.mol

Synonyms:HMS559P11;N-methyl-3-acetyl-4-hydroxy-quinolin-2-one;3-acet4yl-4-hydroxy-1-methyl-2(1H)-quinolinone;3-acetyl-4-hydroxy-1-methylquinoline-2(1H)-one;3-Acetyl-4-hydroxy-1-methyl-2(1H)-quinolinone;3-acetyl-4-hydroxy-1-methylquinolin-2(1H)-one;2(1H)-quinolinone,3-acetyl-4-hydroxy-1-methyl;3-acetyl-4-hydroxyl-1-methylquinolin-2(1H)-one;3-acetyl-4-hydroxy-1-methyl-2-oxohydroquinoline;1-methyl-3-acetyl-4-hydroxyquinolin-2(1H)-one;3-acetyl-4-hydroxy-1-methyl-2H-(1)-quinolin-2-one;

Chemical Property of 3-ACETYL-4-HYDROXY-1-METHYL-2(1H)-QUINOLINONE

Chemical Property:

• Melting Point: 143-145 °C(Solv: ethanol (64-17-5))
• Boiling Point: 167-172 °C(Press: 4-5 Torr)
• PKA: 4.50±1.00(Predicted)
• PSA: 59.30000
• Density: 1.346±0.06 g/cm3(Predicted)
• LogP: 1.44670

Purity/Quality:

99% ^*data from raw suppliers

3-Acetyl-4-hydroxy-1-methyl-2(1H)-quinolinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-ACETYL-4-HYDROXY-1-METHYL-2(1H)-QUINOLINONE

There total 15 articles about 3-ACETYL-4-HYDROXY-1-METHYL-2(1H)-QUINOLINONE 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%

4-hydroxy-3-acetyl-1H-quinoline-2-one (26138-64-7) + methyl iodide (74-88-4) → 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone (54289-76-8)

Guidance literature:

With potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 24h; regioselective reaction;

DOI:10.1007/s10593-016-1885-8

Reference yield: 93.0%

4-Hydroxy-6-methyl-5,6-dihydro-2,5-dioxo-2H-pyrano<3,2-c>quinoline (18706-63-3) → 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone (54289-76-8)

Guidance literature:

With sodium hydroxide; In water; ethylene glycol; for 1h; Heating;

Reference yield: 83.0%

6-methyl-4-methylamino-pyrano<3,2-c>quinolin-2,5(6H)-dione (71509-15-4) → 3-acetyl-4-hydroxy-1-methyl-2(1H)-quinolone (54289-76-8)

Guidance literature:

With potassium hydroxide; Heating;

DOI:10.1002/prac.19943360707

upstream raw materials:

4-Hydroxy-6-methyl-5,6-dihydro-2,5-dioxo-2H-pyrano<3,2-c>quinoline

6-methyl-4-methylamino-pyrano<3,2-c>quinolin-2,5(6H)-dione

4-hydroxy-3-acetyl-1H-quinoline-2-one

methyl iodide

Downstream raw materials:

2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-(4-methoxy-phenyl)-4H-pyran-3-carbonitrile

2-Amino-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4-phenyl-4H-pyran-3-carbonitrile

2-Amino-4-(4-chloro-phenyl)-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4H-pyran-3-carbonitrile

2-Amino-4-(4-chloro-phenyl)-6-(4-hydroxy-1-methyl-2-oxo-1,2-dihydro-quinolin-3-yl)-4H-pyran-3-carboxylic acid ethyl ester

Refernces

• 1、 Kumar, Devadoss Karthik,Rajkumar, Rayappan,Rajendran, Subramaniam Parameswaran. "Robust synthesis of linear and angular furoquinolines using Rap–stoermer reaction". . p. 322 - 325. Retrieved 2016.
• 2、 Elgogary, Sameh,Abd Elghafar, Hoda,Mashaly, Mohammad. "Synthesis, photooxygenation, and characterization of new angular furoquinolinone derivatives, a new furocoumarin bioisoster". . p. 1082 - 1089. Retrieved 2021/02/01.
• 3、 Brawley, Jhonnathan,Etter, Emily,Heredia, Dante,Intasiri, Amarawan,Nennecker, Kyle,Smith, Joshua,Welcome, Brandon M.,Brizendine, Richard K.,Gould, Thomas W.,Bell, Thomas W.,Cremo, Christine. "Synthesis and Evaluation of 4-Hydroxycoumarin Imines as Inhibitors of Class II Myosins". . p. 11131 - 11148. Retrieved 2020/11/09.