3-(3,4-Dihydro-4-methyl-3-oxoquinoxalin-2-yl)propionic acid, 3-(2-Carboxyethyl)-1,2-dihydro-1-methyl-2-oxoquinoxaline

Base Information

• Chemical Name: 3-(3,4-Dihydro-4-methyl-3-oxoquinoxalin-2-yl)propionic acid, 3-(2-Carboxyethyl)-1,2-dihydro-1-methyl-2-oxoquinoxaline
• CAS No.: 1501-38-8
• Molecular Formula: C₁₂H₁₂N₂O₃
• Molecular Weight: 232.239
• Hs Code.: 2933990090
• Mol file: 1501-38-8.mol

Synonyms:2-Quinoxalinepropionicacid, 3,4-dihydro-4-methyl-3-oxo- (7CI,8CI); NSC 75194

Chemical Property of 3-(3,4-Dihydro-4-methyl-3-oxoquinoxalin-2-yl)propionic acid, 3-(2-Carboxyethyl)-1,2-dihydro-1-methyl-2-oxoquinoxaline

Chemical Property:

• Vapor Pressure: 8.3E-09mmHg at 25°C
• Melting Point: 180-182 °C
• Boiling Point: 447.9°Cat760mmHg
• PKA: 4.36±0.10(Predicted)
• Flash Point: 224.7°C
• PSA: 72.19000
• Density: 1.32g/cm³
• LogP: 0.95070

Purity/Quality:

99%min ^*data from raw suppliers

3-(1-Methyl-2-oxo-1,2-dihydroquinoxalin-3-yl)propionic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-(3,4-Dihydro-4-methyl-3-oxoquinoxalin-2-yl)propionic acid, 3-(2-Carboxyethyl)-1,2-dihydro-1-methyl-2-oxoquinoxaline

There total 6 articles about 3-(3,4-Dihydro-4-methyl-3-oxoquinoxalin-2-yl)propionic acid, 3-(2-Carboxyethyl)-1,2-dihydro-1-methyl-2-oxoquinoxaline 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: 58.0%

ethyl 3-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate → 3-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)propanoic acid (1501-38-8)

Guidance literature:

With lithium hydroxide monohydrate; In tetrahydrofuran; ethanol; water; at 20 ℃; for 4h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b00933

Reference yield:

α-ketoglutaric acid (328-50-7) → 3-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)propanoic acid (1501-38-8)

Guidance literature:

Multi-step reaction with 4 steps

1: acetyl chloride / 2.5 h / 0 °C / Inert atmosphere

2: ethanol / 16 h / 20 °C / Inert atmosphere; Reflux

3: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

4: lithium hydroxide monohydrate / ethanol; tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; potassium carbonate; acetyl chloride; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.7b00933

Reference yield:

diethyl 2-ketoglutarate (5965-53-7) → 3-(4-methyl-3-oxo-3,4-dihydroquinoxalin-2-yl)propanoic acid (1501-38-8)

Guidance literature:

Multi-step reaction with 3 steps

1: ethanol / 16 h / 20 °C / Inert atmosphere; Reflux

2: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C / Inert atmosphere

3: lithium hydroxide monohydrate / ethanol; tetrahydrofuran; water / 4 h / 20 °C / Inert atmosphere

With lithium hydroxide monohydrate; potassium carbonate; In tetrahydrofuran; ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.7b00933

upstream raw materials:

ethyl 3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propanoate

α-ketoglutaric acid

diethyl 2-ketoglutarate

3-(3-oxo-3,4-dihydroquinoxalin-2-yl)propionic acid ethyl ester

Refernces

• 1、 Ferreira De Freitas, Renato,Harding, Rachel J.,Franzoni, Ivan,Ravichandran, Mani,Mann, Mandeep K.,Ouyang, Hui,Lautens, Mark,Santhakumar, Vijayaratnam,Arrowsmith, Cheryl H.,Schapira, Matthieu. "Identification and Structure-Activity Relationship of HDAC6 Zinc-Finger Ubiquitin Binding Domain Inhibitors". supporting information. p. 4517 - 4527. Retrieved 2018/05/31.