2,6-Dimethyl-4-phenyl-nicotinic acid ethyl ester

Base Information

• Chemical Name: 2,6-Dimethyl-4-phenyl-nicotinic acid ethyl ester
• CAS No.: 4350-44-1
• Molecular Formula: C16H17NO2
• Molecular Weight: 255.316
• DSSTox Substance ID: DTXSID30465168
• Nikkaji Number: J1.395.177B
• Wikidata: Q82290918
• Mol file: 4350-44-1.mol

Synonyms:4350-44-1;2,6-DIMETHYL-4-PHENYL-NICOTINIC ACID ETHYL ESTER;SCHEMBL2510353;DTXSID30465168;ETHYL 2,6-DIMETHYL-4-PHENYLPYRIDINE-3-CARBOXYLATE;OQVGXASMCWLVHD-UHFFFAOYSA-N;AKOS015964219;ethyl 2,6-dimethyl-4-phenylnicotinate

Chemical Property of 2,6-Dimethyl-4-phenyl-nicotinic acid ethyl ester

Chemical Property:

• Boiling Point: 147 °C(Press: 1.5 Torr)
• PKA: 4.89±0.18(Predicted)
• Density: 1.086±0.06 g/cm3(Predicted)
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 4
• Exact Mass: 255.125928785
• Heavy Atom Count: 19
• Complexity: 299

Purity/Quality:

99%min ^*data from raw suppliers

2,6-DIMETHYL-4-PHENYL-NICOTINIC ACID ETHYL ESTER 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=C(C=C(N=C1C)C)C2=CC=CC=C2

Technology Process of 2,6-Dimethyl-4-phenyl-nicotinic acid ethyl ester

There total 10 articles about 2,6-Dimethyl-4-phenyl-nicotinic acid ethyl 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: 86.0%

[((E)-4-phenylbut-3-en-2-ylidene)amino]hydroxide (61210-87-5) + ethyl acetoacetate (141-97-9) → ethyl 2,6-dimethyl-4-phenylpyridine-3-carboxylate (4350-44-1)

Guidance literature:

With cerium(III) chloride; sodium iodide; at 150 - 160 ℃; for 3.5h;

Reference yield: 80.0%

ethyl acetoacetate (141-97-9) + 4-phenyl-3-butyne-2-one (1817-57-8) → ethyl 2,6-dimethyl-4-phenylpyridine-3-carboxylate (4350-44-1)

Guidance literature:

With ammonium acetate; acetic acid; In toluene; for 20h; Heating;

DOI:10.1021/jo048106q

Reference yield: 71.0%

ethyl aminocrotonate (626-34-6,7318-00-5,41867-20-3) + 4-phenyl-3-butyne-2-one (1817-57-8) → ethyl 2,6-dimethyl-4-phenylpyridine-3-carboxylate (4350-44-1)

Guidance literature:

With Amberlyst 15; In toluene; at 50 ℃;

DOI:10.1055/s-2001-15140

upstream raw materials:

iodobenzene

ethyl 4-iodo-2,6-dimethyl-3-pyridinecarboxylate

[((E)-4-phenylbut-3-en-2-ylidene)amino]hydroxide

ethyl acetoacetate

Downstream raw materials:

N-[3,5-bis(trifluoromethyl)benzyl]-2,6-dimethyl-4-phenylnicotinamide

N-[3,5-bis(trifluoromethyl)benzyl]-4-phenyl-N,2,6-trimethylnicotinamide

2,6-dimethyl-4-phenylnicotinic acid

2-butyl-5-((2,6-dimethyl-4-phenylpyridin-3-ylmethyl)amino)isoindolin-1-one

Refernces

• 1、 Yamamoto, Shun-Ichi,Okamoto, Kana,Murakoso, Makiko,Kuninobu, Yoichiro,Takai, Kazuhiko. "Rhenium-catalyzed regioselective synthesis of multisubstituted pyridines from β-enamino ketones and alkynes via C-C bond cleavage". supporting information; experimental part. p. 3182 - 3185. Retrieved 2012/07/28.
• 2、 Kumar, Sanjay,Saini, Anil,Sandhu, Jagir S.. "Cerium catalysed Michael addition to α,β-unsaturated oximes: A facile and efficient synthesis of substituted pyridines". . p. 429 - 432. Retrieved 2007/10/03.