Ethyl 2-((2-methyl-3-(trifluoromethyl)phenyl)amino)nicotinate

Base Information

• Chemical Name: Ethyl 2-((2-methyl-3-(trifluoromethyl)phenyl)amino)nicotinate
• CAS No.: 54396-42-8
• Molecular Formula: C16H15F3N2O2
• Molecular Weight: 324.303
• UNII: 6XBM1LQY7H
• Mol file: 54396-42-8.mol

Synonyms:Flunixin ethyl ester;UNII-6XBM1LQY7H;6XBM1LQY7H;54396-42-8;Flunixin ethyl ester [USP];Ethyl 2-((2-methyl-3-(trifluoromethyl)phenyl)amino)nicotinate;3-Pyridinecarboxylic acid, 2-((2-methyl-3-(trifluoromethyl)phenyl)amino)-, ethyl ester;O-Ethyl Flunixin;Ethyl 2-[[2-Methyl-3-(trifluoromethyl)phenyl]amino]pyridine-3-carboxylate (Flunixin Ethyl Ester);Flunixin Meglumine Imp. D (EP);2-[[2-Methyl-3-(trifluoromethyl)phenyl]amino]-3-pyridinecarboxylic acid ethyl ester;Flunixin Meglumine Impurity D;Flunixin Impurity D;SCHEMBL9457265;WICOBQMQNHKGTO-UHFFFAOYSA-N;CID 11120881;FLUNIXIN MEGLUMINE IMPURITY D [EP IMPURITY];ethyl 2-[2-methyl-3-(trifluoromethyl)anilino]pyridine-3-carboxylate

Chemical Property of Ethyl 2-((2-methyl-3-(trifluoromethyl)phenyl)amino)nicotinate

Chemical Property:

• Boiling Point: 143 - 146 °C (0.1 mmHg)
• PSA: 51.22000
• LogP: 4.40210
• XLogP3: 4.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 5
• Exact Mass: 324.10856221
• Heavy Atom Count: 23
• Complexity: 403

Purity/Quality:

HPLC ≥ 98% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N=CC=C1)NC2=CC=CC(=C2C)C(F)(F)F
• Uses: O-Ethyl Flunixin is an impurity of Flunixin Meglumine (F455400), a cyclooxigenase inhibitor. Anti-inflammatory; analgesic; antipyretic.

Technology Process of Ethyl 2-((2-methyl-3-(trifluoromethyl)phenyl)amino)nicotinate

There total 5 articles about Ethyl 2-((2-methyl-3-(trifluoromethyl)phenyl)amino)nicotinate 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: 86.0%

2-methyl-3-trifluoromethylaniline (54396-44-0) + ethyl 2-chloronicotinate (1452-94-4) → ethyl 2-(2-methyl-3-trifluoromethylanilino)nicotinate (54396-42-8)

Guidance literature:

In ethylene glycol; at 160 ℃; for 6h;

DOI:10.3987/COM-94-6822

Reference yield:

N-(3-(trifluoromethyl)phenyl)pivalamide (1939-19-1) → ethyl 2-(2-methyl-3-trifluoromethylanilino)nicotinate (54396-42-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) BuLi / 1.) ether, hexane, 4 h, 2.) ether, hexane, overnight

2: 78.3 percent / KOH / ethane-1,2-diol / 8 h / 160 °C

3: 86 percent / ethane-1,2-diol / 6 h / 160 °C

With potassium hydroxide; n-butyllithium; In ethylene glycol;

DOI:10.3987/COM-94-6822

Reference yield:

3-trifluoromethylaniline (98-16-8) → ethyl 2-(2-methyl-3-trifluoromethylanilino)nicotinate (54396-42-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 93 percent / K₂CO₃ / acetone / 6 h / Heating

2: 1.) BuLi / 1.) ether, hexane, 4 h, 2.) ether, hexane, overnight

3: 78.3 percent / KOH / ethane-1,2-diol / 8 h / 160 °C

4: 86 percent / ethane-1,2-diol / 6 h / 160 °C

With potassium hydroxide; n-butyllithium; potassium carbonate; In ethylene glycol; acetone;

DOI:10.3987/COM-94-6822

upstream raw materials:

2-methyl-3-trifluoromethylaniline

ethyl 2-chloronicotinate

N-(3-(trifluoromethyl)phenyl)pivalamide

3-trifluoromethylaniline

Downstream raw materials:

flunixin

Refernces