Ethyl 6-chloro-5-cyano-2-methylnicotinate

Base Information

• Chemical Name: Ethyl 6-chloro-5-cyano-2-methylnicotinate
• CAS No.: 64119-42-2
• Molecular Formula: C10H9ClN2O2
• Molecular Weight: 224.647
• Hs Code.: 2933399090
• European Community (EC) Number: 634-695-2
• DSSTox Substance ID: DTXSID50383032
• Nikkaji Number: J2.869.219F
• Wikidata: Q82174582
• Mol file: 64119-42-2.mol

Synonyms:Ethyl 6-chloro-5-cyano-2-methylnicotinate;64119-42-2;ethyl 6-chloro-5-cyano-2-methylpyridine-3-carboxylate;6-Chloro-5-cyano-2-methyl-nicotinic acid ethyl ester;SCHEMBL3227432;DTXSID50383032;QXZBVLFURRXJLB-UHFFFAOYSA-N;MFCD00179894;AKOS015851188;AS-5030;SB38091;CS-0097778;5-carbethoxy-6-methyl-2-chloronicotinonitrile;2-Methyl-5-cyano-6-chloronicotinic acid ethyl ester;ethyl6-chloro-5-cyano-2-methylpyridine-3-carboxylate

Chemical Property of Ethyl 6-chloro-5-cyano-2-methylnicotinate

Chemical Property:

• PSA: 62.98000
• LogP: 2.09178
• Storage Temp.: Inert atmosphere,Room Temperature
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 224.0352552
• Heavy Atom Count: 15
• Complexity: 286

Purity/Quality:

97% ^*data from raw suppliers

Ethyl6-Chloro-5-cyano-2-methylnicotinate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C1=C(N=C(C(=C1)C#N)Cl)C

Technology Process of Ethyl 6-chloro-5-cyano-2-methylnicotinate

There total 6 articles about Ethyl 6-chloro-5-cyano-2-methylnicotinate 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: 98.0%

5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (52600-52-9) → ethyl 6-chloro-5-cyano-2-methylnicotinate (64119-42-2)

Guidance literature:

With oxalyl dichloride; N,N-dimethyl-formamide; In dichloromethane; for 18h; Reflux;

DOI:10.1016/j.ejmech.2013.04.007

Reference yield: 69.0%

6-amino-5-cyano-2-methylnicotinic acid ethyl ester (137522-47-5) → ethyl 6-chloro-5-cyano-2-methylnicotinate (64119-42-2)

Guidance literature:

With copper dichloride; isopentyl nitrite; In acetonitrile; at 65 ℃; for 0.416667h; Inert atmosphere;

DOI:10.1055/s-0030-1258149

Reference yield:

ethyl acetoacetate (141-97-9) → ethyl 6-chloro-5-cyano-2-methylnicotinate (64119-42-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: ethanol / 42 °C

1.2: 30 °C

1.3: 20 - 25 °C / pH 4 - 5

2.1: trichlorophosphate / acetonitrile / 20 h / 80 °C / Inert atmosphere

2.2: Inert atmosphere

With trichlorophosphate; In ethanol; acetonitrile;

DOI:10.1021/op200368m

upstream raw materials:

ethyl 5-cyano-6-hydroxy-2-methyl-pyridine-3-carboxylate

5-Cyano-2-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester

6-amino-5-cyano-2-methylnicotinic acid ethyl ester

ethyl acetoacetate

Downstream raw materials:

ethyl 5-cyano-2-methylnicotinate

5-Cyano-6-(2-methoxy-phenylamino)-2-methyl-nicotinic acid ethyl ester

2-cyclohexylamino-5-carbethoxy-6-methylnicotinonitrile

5-Cyano-2-methyl-6-p-tolylamino-nicotinic acid ethyl ester