5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)nicotinic acid

Base Information

• Chemical Name: 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)nicotinic acid
• CAS No.: 1018782-82-5
• Molecular Formula: C₁₄H₉ClF₃NO₃
• Molecular Weight: 331.679
• Mol file: 1018782-82-5.mol

Synonyms:5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid

Chemical Property of 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)nicotinic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)nicotinic acid

There total 7 articles about 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)nicotinic acid 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: 95.0%

6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid (1012792-56-1) + 2,2,2-trifluoroethanol (75-89-8) → 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (1018782-82-5)

Guidance literature:

With potassium hydroxide; In dimethyl sulfoxide; at 100 ℃; for 0.25h; Inert atmosphere; Microwave irradiation;

DOI:10.1021/jm4010708

Reference yield:

5-bromo-6-hydroxy-3-pyridinecarboxylic acid (41668-13-7) → 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (1018782-82-5)

Guidance literature:

Multi-step reaction with 5 steps

1: trichlorophosphate; quinoline / 2 h / 120 °C / Inert atmosphere

2: dichloromethane / 1.25 h / 70 °C / Inert atmosphere

3: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / toluene; water / 1 h / 90 °C / Inert atmosphere

4: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / Inert atmosphere; Reflux

5: potassium hydroxide / dimethyl sulfoxide / 0.25 h / 100 °C / Inert atmosphere; Microwave irradiation

With quinoline; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; lithium hydroxide monohydrate; sodium carbonate; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1021/jm4010708

Reference yield:

6-hydroxy-3-pyridinecarboxylic acid (5006-66-6) → 5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-3-pyridinecarboxylic acid (1018782-82-5)

Guidance literature:

Multi-step reaction with 6 steps

1: acetic acid; bromine / 18.75 h / 45 - 50 °C / Inert atmosphere

2: trichlorophosphate; quinoline / 2 h / 120 °C / Inert atmosphere

3: dichloromethane / 1.25 h / 70 °C / Inert atmosphere

4: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium carbonate / toluene; water / 1 h / 90 °C / Inert atmosphere

5: lithium hydroxide monohydrate / water; tetrahydrofuran / 1 h / Inert atmosphere; Reflux

6: potassium hydroxide / dimethyl sulfoxide / 0.25 h / 100 °C / Inert atmosphere; Microwave irradiation

With quinoline; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; lithium hydroxide monohydrate; bromine; sodium carbonate; acetic acid; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; dichloromethane; water; dimethyl sulfoxide; toluene;

DOI:10.1021/jm4010708

upstream raw materials:

5-bromo-6-hydroxy-3-pyridinecarboxylic acid

6-hydroxy-3-pyridinecarboxylic acid

5-bromo-6-chloro-3-pyridinecarboxylic acid methyl ester

6-chloro-5-(4-chlorophenyl)-3-pyridinecarboxylic acid

Downstream raw materials:

5-(4-chlorophenyl)-6-(2,2,2-trifluoroethoxy)-N'-(2,2,2-trifluoroethyl)-3-pyridinecarboxylic acid hydrazide

Refernces

• 1、 -. "3-Pyridinecarboxamide derivatives as HDL-cholesterol raising agents". Page/Page column 28. . Retrieved 2008/06/13.