6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE

Base Information

• Chemical Name: 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE
• CAS No.: 1140-81-4
• Molecular Formula: C₁₂H₁₂N₂O₂
• Molecular Weight: 216.239
• Hs Code.: 2933499090
• Mol file: 1140-81-4.mol

Synonyms:4-Quinolinol,6-acetamido-2-methyl- (6CI,7CI,8CI);acetamide, N-(1,4-dihydro-2-methyl-4-oxo-6-quinolinyl)-;acetamide, N-(4-hydroxy-2-methyl-6-quinolinyl)-;N-(2-methyl-4-oxo-1,4-dihydroquinolin-6-yl)acetamide;

Chemical Property of 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE

Chemical Property:

• Vapor Pressure: 5.19E-08mmHg at 25°C
• Melting Point: >300 °C
• Refractive Index: 1.615
• Boiling Point: 442 °C at 760 mmHg
• PKA: 4.29±0.40(Predicted)
• Flash Point: 191.6 °C
• PSA: 62.22000
• Density: 1.248 g/cm³
• LogP: 2.28020
• Solubility.: Ethyl Acetate; Toluene

Purity/Quality:

98%,99%, ^*data from raw suppliers

N-(4-Hydroxy-2-methyl-6-quinolinyl)acetamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: N-(4-Hydroxy-2-methyl-6-quinolinyl)acetamide is an intermediate in the synthesis of NSC 23766 (N900280), which is a highly soluble and membrane permeable Rac GTPase inhibitor. NSC 23766 inhibits Rac GTPase by targeting Rac activation by guanine nucleotide exchange factor (GEF). NSC 23766 has been shown to inhibit the anchorage-independent growth and invasion phenotypes of human prostate cancer PC-3 cells.

Technology Process of 6-ACETAMIDO-4-HYDROXY-2-METHYLQUINOLINE

There total 8 articles about 6-ACETAMIDO-4-HYDROXY-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: 88.0%

methyl 3-{[4-(acetylamino) phenyl]amino}but-2-enoate (244219-89-4) → N-(4-hydroxy-2-methylquinolin-6-yl)acetamide (1140-81-4)

Guidance literature:

In diphenylether; at 245 - 260 ℃; for 0.25h;

Reference yield: 88.0%

methyl 3-(4-acetylaminophenylamino)crotonate → N-(4-hydroxy-2-methylquinolin-6-yl)acetamide (1140-81-4)

Guidance literature:

In various solvent(s); at 280 ℃; for 0.166667h;

DOI:10.1021/jm0002073

Reference yield: 88.0%

→ N-(4-hydroxy-2-methylquinolin-6-yl)acetamide (1140-81-4)

Guidance literature:

upstream raw materials:

6-amino-2-methylquinolin-4-ol

acetic anhydride

(E)-ethyl 3-((4-acetamidophenyl)amino)but-2-enoate

N-acetyl-p-phenylenediamine

Downstream raw materials:

N-(4-methoxy-2-methyl-6-quinolyl)acetamide

6-amino-2-methylquinolin-4-ol

6-acetamide-4-chloro-2-methylquinoline

Refernces

• 1、 Weiss, Ryan J.,Gordts, Philip L. S. M.,Le, Dzung,Xu, Ding,Esko, Jeffrey D.,Tor, Yitzhak. "Small molecule antagonists of cell-surface heparan sulfate and heparin-protein interactions". . p. 5984 - 5993. Retrieved 2015/09/28.
• 2、 -. "GTPASE INHIBITORS AND USE THEREOF FOR CONTROLLING PLATELET HYPERACTIVITY". Page/Page column 42. . Retrieved 2008/06/13.