2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester

Base Information

• Chemical Name: 2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester
• CAS No.: 1175086-67-5
• Molecular Formula: C₁₆H₁₅ClFNO₂
• Molecular Weight: 307.752
• Mol file: 1175086-67-5.mol

Synonyms:2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester

Chemical Property of 2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester

There total 7 articles about 2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester 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: 89.0%

methanol (67-56-1) + lumiracoxib (220991-20-8) → 2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester (1175086-67-5)

Guidance literature:

methanol; lumiracoxib; With hydrogenchloride; In water; for 8h; Reflux;

With sodium carbonate; In water;

Reference yield:

2-Amino-5-methylbenzoic acid (2941-78-8) → 2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester (1175086-67-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) acetate monohydrate / 1,4-dioxane / 25 °C

2: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

3: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C

4: dimethyl sulfoxide / 1.5 h / Inert atmosphere

5: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere

6: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C

With pyridine; dmap; thionyl chloride; dimethylsulfide borane complex; water; copper(II) acetate monohydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; barium(II) hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; 1: |Chan-Lam Coupling;

DOI:10.1002/cmdc.201200272

Reference yield:

(2-chloro-6-fluorophenyl)boronic acid (313545-32-3) → 2-[(2-chloro-6-fluorophenyl)amino]-5-methylbenzeneacetic acid methyl ester (1175086-67-5)

Guidance literature:

Multi-step reaction with 6 steps

1: 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(II) acetate monohydrate / 1,4-dioxane / 25 °C

2: dimethylsulfide borane complex / tetrahydrofuran / 0 °C / Inert atmosphere; Reflux

3: pyridine; thionyl chloride / tetrahydrofuran / 0 - 5 °C

4: dimethyl sulfoxide / 1.5 h / Inert atmosphere

5: water; barium(II) hydroxide / 1,4-dioxane / 30 h / Reflux; Inert atmosphere

6: dmap; dicyclohexyl-carbodiimide / dichloromethane / 0 - 20 °C

With pyridine; dmap; thionyl chloride; dimethylsulfide borane complex; water; copper(II) acetate monohydrate; 1,8-diazabicyclo[5.4.0]undec-7-ene; dicyclohexyl-carbodiimide; barium(II) hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; dimethyl sulfoxide; 1: |Chan-Lam Coupling;

DOI:10.1002/cmdc.201200272

upstream raw materials:

methanol

lumiracoxib

2-Amino-5-methylbenzoic acid

(2-chloro-6-fluorophenyl)boronic acid

Downstream raw materials:

C₁₅H₁₄ClFN₂O₂

C₁₆H₁₃ClFN₃O₂

Refernces

• 1、 -. "PHTHALIMIDE DERIVATIVES OF NON-STEROIDAL ANTI-INFLAMMATORY COMPOUNDS AND/OR TNF-ALPHA MODULATORS, METHOD FOR PRODUCING SAME, PHARMACEUTICAL COMPOSITIONS CONTAINING SAME AND USES THEREOF FOR THE TREATMENT OF INFLAMMATORY DISEASES". Page/Page column 47. . Retrieved 2012/05/20.