Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

Base Information

• Chemical Name: Methyl 4-chloro-7-methoxyquinoline-6-carboxylate
• CAS No.: 205448-66-4
• Molecular Formula: C12H10ClNO3
• Molecular Weight: 251.669
• Hs Code.: 2933499090
• Mol file: 205448-66-4.mol

Synonyms:6-Quinolinecarboxylic acid,4-chloro-7-methoxy-,methyl ester;methyl 4-chloro-7-methoxyquinoline-6-carboxylate;

Chemical Property of Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

Chemical Property:

• Boiling Point: 377.4±37.0 °C(Predicted)
• PKA: 2.98±0.30(Predicted)
• PSA: 48.42000
• Density: 1.320±0.06 g/cm3(Predicted)
• LogP: 2.68340
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

99% ^*data from raw suppliers

Methyl-4-Chloro-7-methoxyquinoline-6-carboxylate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: Methyl-4-Chloro-7-methoxyquinoline-6-carboxylate is used pharmaceutically for treating infection after burns. It is also used as reagents in the preparation of naphthamides as inhibitors of vascular endothelial growth factor (VEGF) receptor tyrosine kinase.

Technology Process of Methyl 4-chloro-7-methoxyquinoline-6-carboxylate

There total 8 articles about Methyl 4-chloro-7-methoxyquinoline-6-carboxylate 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: 94.53%

7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid methyl ester (205448-65-3) → methyl 4-chloro-7-methoxyquinoline-6-carboxylate (205448-66-4)

Guidance literature:

With trichlorophosphate; In toluene; at 25 - 95 ℃;

Reference yield: 92.8%

methyl 4-hydroxy-7-methoxyquinoline-6-carboxylate → methyl 4-chloro-7-methoxyquinoline-6-carboxylate (205448-66-4)

Guidance literature:

With thionyl chloride; at 100 ℃; for 5h; Temperature;

Reference yield:

7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid methyl ester (205448-65-3) + dichloromethane (75-09-2) → methyl 4-chloro-7-methoxyquinoline-6-carboxylate (205448-66-4)

Guidance literature:

7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid methyl ester; In dimethyl sulfoxide; N,N-dimethyl-formamide; at 125 ℃; for 3h;

dichloromethane; With sodium hydrogencarbonate; at 20 - 25 ℃; Solvent; Temperature;

upstream raw materials:

7-methoxy-4-oxo-1,4-dihydroquinoline-6-carboxylic acid methyl ester

N-methyl-p-aminophenol

Methyl 4-amino-2-methoxybenzoate

methyl 4-(((2,2-dimethyl-4,6-dioxo-1,3-dioxan-5-ylidene)methyl)-amino)-2-methoxybenzoate

Downstream raw materials:

methyl 4-(4-amino-3-chlorophenoxy)-7-methoxy-6-quinolinecarboxylate

methyl 4-(4-amino-3-methylphenoxy)-7-methoxy-6-quinolinecarboxylate

methyl 4-(4-nitro-3-fluorophenoxy)-7-methoxy-6-quinolinecarboxylate

4-[3-chloro-4-(cyclopropylaminocarbonyl)aminophenoxy]-7-methoxy-6-quinoline-carboxamide methanesulfonate

Refernces

• 1、 -. "Lenvatinib impurity as well as preparation method and application thereof". Paragraph 0030; 0037-0040. . Retrieved 2020/07/24.
• 2、 -. "NOVEL POLYMORPHS OF 4-[3-CHLORO-4-(N'-CYCLOPROPYL UREIDO)PHENOXY]-7-METHOXYQUINOLINE-6-CARBOXAMIDE, ITS SALTS AND PROCESS FOR THE PREPARATION THEREOF". Page/Page column 26; 27; 30. . Retrieved 2019/06/23.