6-Chloro-2-hydroxy-4-methylquinoline

Base Information

• Chemical Name: 6-Chloro-2-hydroxy-4-methylquinoline
• CAS No.: 2585-04-8
• Molecular Formula: C₁₀H₈ClNO
• Molecular Weight: 193.633
• Hs Code.: 2933790090
• Mol file: 2585-04-8.mol

Synonyms:6-Chloro-2-hydroxy-4-methylquinoline;6-Chloro-4-methylquinolin-2(1H)-one;6-CHLORO-4-METHYLQUINOLIN-2(1H)-OL;2-Hydroxy-4-Methyl-6-chloroquinoline

Chemical Property of 6-Chloro-2-hydroxy-4-methylquinoline

Chemical Property:

• Vapor Pressure: 5.92E-06mmHg at 25°C
• Refractive Index: 1.587
• Boiling Point: 379.3 °C at 760 mmHg
• Flash Point: 183.2 °C
• PSA: 33.12000
• Density: 1.273 g/cm³
• LogP: 2.90220
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

6-Chloro-4-methylquinolin-2(1H)-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 6-Chloro-2-hydroxy-4-methylquinoline

There total 12 articles about 6-Chloro-2-hydroxy-4-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: 76.0%

ethyl acetoacetate (141-97-9) + 4-chloro-aniline (106-47-8) → 6-chloro-4-methylquinolin-2(1H)-one (2585-04-8)

Guidance literature:

With toluene-4-sulfonic acid; for 0.0666667h; microwave irradiation;

Reference yield: 73.0%

carbon dioxide (124-38-9,18923-20-1) + 4-chloro-2-(prop-1-en-2-yl)aniline (720681-64-1) → 6-chloro-4-methylquinolin-2(1H)-one (2585-04-8)

Guidance literature:

With sodium t-butanolate; In diethylene glycol dimethyl ether; at 140 ℃; for 24h; under 760.051 Torr; Glovebox; Schlenk technique;

DOI:10.1002/anie.201602095

Reference yield: 70.0%

4'-Chloroacetoacetanilide (101-92-8) → 6-chloro-4-methylquinolin-2(1H)-one (2585-04-8)

Guidance literature:

With iron(III) oxide; In acetonitrile; at 80 ℃; for 12h; Sealed tube; Green chemistry;

DOI:10.1016/j.tetlet.2020.152535

upstream raw materials:

4'-Chloroacetoacetanilide

(6-chloro-2-hydroxy-[4]quinolyl)-acetic acid

3-oxo-glutaric acid bis-(4-chloro-anilide)

4-chloro-aniline

Downstream raw materials:

6-chloro-4-methyl-2-chloroquinoline

6-chloro-2-hydroxy-quinoline-4-carboxylic acid

6-Chloro-4-methyl-2-oxo-2H-quinoline-1-carboxylic acid [1-(2,4-dichloro-phenyl)-meth-(E)-ylidene]-hydrazide

1-(4-nitrobenzylidenehydrazido)-6-chloro-4-methylquinolin-2-one

Refernces

• 1、 Azad, Rajaram,Karnik, Kshipra S.,Sarkate, Aniket P.,Tiwari, Shailee V.,Wakte, Pravin S.. "Free energy perturbation guided Synthesis with Biological Evaluation of Substituted Quinoline derivatives as small molecule L858R/T790M/C797S mutant EGFR inhibitors targeting resistance in Non-Small Cell Lung Cancer (NSCLC)". . . Retrieved 2021/08/09.
• 2、 Kabi, Arup K.,Gujjarappa, Raghuram,Vodnala, Nagaraju,Kaldhi, Dhananjaya,Tyagi, Ujjawal,Mukherjee, Kalisadhan,Malakar, Chandi C.. "HFIP-mediated strategy towards β-oxo amides and subsequent Friedel-Craft type cyclization to 2?quinolinones using recyclable catalyst". . . Retrieved 2020/10/20.