1620-75-3

Usage

Uses

Used in Pharmaceutical Industry:
6-Methylpyridine-2-carbonitrile is used as an intermediate in the preparation of selective cyclooxygenase-2 (COX-2) inhibitors. These inhibitors are important in the development of anti-inflammatory and pain-relieving drugs, as they help reduce inflammation and pain without causing the side effects associated with non-selective COX inhibitors.
6-Methylpyridine-2-carbonitrile is also used as an intermediate in the synthesis of calcium antagonists. Calcium antagonists are a class of drugs that block the movement of calcium ions across cell membranes, which can help in the treatment of various cardiovascular diseases, such as hypertension, angina, and arrhythmias.
Used in Chemical Research and Development:
6-Methyl-2-pyridinecarbonitrile was used in the synthesis of zinc complexes bearing N,N′-bidentate entiopure ligands. These complexes have potential applications in various fields, including catalysis, coordination chemistry, and materials science. The development of novel zinc complexes can lead to advancements in these areas and contribute to the creation of new technologies and products.

Synthesis Reference(s)

The Journal of Organic Chemistry, 48, p. 1375, 1983 DOI: 10.1021/jo00156a053

InChI:InChI=1/C7H6N2/c1-6-3-2-4-7(5-8)9-6/h2-4H,1H3

Upstream product

• 18368-63-3 6-chloro-2-picoline 
• 151-50-8 potassium cyanide 
• 92304-51-3 N-Methoxy-2-picolinium iodide 
• 931-19-1 2-methylpyridine N-oxide 
• 7677-24-9 trimethylsilyl cyanide 
• 143-33-9 sodium cyanide 
• 5315-25-3 2-bromo-6-methylpyridine 
• 1195-40-0 6-methyl-2-pyridinecarboxaldehyde oxime 
• 557-21-1 dicyanozinc 
• 1122-72-1 6-methyl-2-pyridinecarboxaldehyde 
• 557-21-1 zinc(II) cyanide 
• 109-06-8 α-picoline 
• 288-36-8 1,2,3-triazole 
• 717843-48-6 3-bromo-6-methylpyridine-2-carbonitrile 

Downstream Products

• 5933-30-2 6-Methylpyridine-2-carbothiamide 
• 87884-49-9 6-methylpyridine-2-carboxylic acid hydrochlorid salt 
• 85148-97-6 6-Dibromomethyl-2-cyanopyridine 
• 199277-70-8 (S)-4-isopropyl-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole 
• 199277-77-5 (S)-4-benzyl-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazoline 
• 199277-73-1 (R)-2-(6-methylpyridin-2-yl)-4-phenyl-4,5-dihydrooxazole 
• 199277-80-0 (S)-4-(tert-butyl)-2-(6-methylpyridin-2-yl)-4,5-dihydrooxazole 
• 177660-81-0 2-methyl-6-(1-(4-(methylsulfonyl)phenyl)-4-(trifluoromethyl)-1H-imidazol-2-yl)-pyridine 
• 50501-38-7 6-(hydroxymethyl)pyridine-2-carbonitrile 
• 108337-76-4 2,6-dimethyl-4-(6-cyano-2-pyridyl)-1,4-dihydropyridine-3,5-dicarboxylic acid 3-β-(N-benzyl-N-methylamino)ethyl ester 5-methyl ester 
• 89115-89-9 cis-6-methylpipecolinic acid 
• 10273-88-8 3-methyl-2,2'-bipyridine 
• 112736-11-5 6-methyl-2-pyridinecarboximidamide monohydrochloride 
• 149928-83-6 6-cyano-2-(2-oxo-2-phenylethyl)-pyridine 

Relevant academic research and scientific papers

Enantioselective Ni-Catalyzed Electrochemical Synthesis of Biaryl Atropisomers

A scalable enantioselective nickel-catalyzed electrochemical reductive homocoupling of aryl bromides has been developed, affording enantioenriched axially chiral biaryls in good yield under mild conditions using electricity as a reductant in an undivided cell. Common metal reductants such as Mn or Zn powder resulted in significantly lower yields in the absence of electric current under otherwise identical conditions, underscoring the enhanced reactivity provided by the combination of transition metal catalysis and electrochemistry.

Method for preparing aryl primary amide by adopting metal-catalyzed one-pot method

The invention discloses a method for synthesizing aryl primary amide by adopting a metal-catalyzed one-pot method. The method comprises the steps of: taking aryl bromidess as raw materials, allowing the aryl bromidess to react with a cyanide source under the action of a palladium catalyst, substituting bromine on an aromatic ring with cyano to obtain cyano aromatic hydrocarbon, directly adding anaqueous solution of alkali into the reaction solution without aftertreatment, and carrying out hydrolysis reaction to obtain aryl primary amide. Compared with the prior art, the method for preparing aryl primary amide from the aryl bromides has the advantages of the short synthesis route, fewer reaction steps, simple operation, mild conditions, the high conversion rate, low toxicity and industrialproduction potential.

Nanocrystalline CeO2 as a Highly Active and Selective Catalyst for the Dehydration of Aldoximes to Nitriles and One-Pot Synthesis of Amides and Esters

The dehydration of aldoximes into nitriles has been performed in the presence of various metal oxides with different acid-base properties (Al2O3, TiO2, CeO2, MgO). The results showed that a nanocrystalline CeO2 was the most active catalyst. An in situ IR spectroscopy study supports a polar elimination mechanism in the dehydration of aldoxime on metal oxide catalysts, in which Lewis acid sites and basic sites are involved. The Lewis acid sites intervene in the adsorption of the oxime on the catalyst surface while surface base sites are responsible for the C1-H bond cleavage. Thus, the acid-base properties of nanocrystalline CeO2 are responsible for the high catalytic activity and selectivity. A variety of aldoximes including alkyl and cycloalkyl aldoximes have been dehydrated into the corresponding nitriles in good yields (80-97%) using nanosized ceria which moreover resulted in a stable and reusable catalyst. Additionally, it has been showed that a variety of pharmacologically important products such as picolinamide and picolinic acid alkyl ester derivatives can be obtained in good yields from 2-pyridinaldoxime in a one-pot process using the nanoceria as catalyst.

A 2-cyano-6-methyl pyridine preparation method (by machine translation)

The aim of the invention is to overcome the defects in the prior art, provides a 2-cyano-6-methyl pyridine preparation method, which belongs to the technical field of synthesis of pharmaceutical intermediates. The method is, will hydrobromidum and 2-amino-6-methyl pyridine mixed, heat insulation; and then cooling the solution, adding to the solution bromine Br 2, then maintain the low-temperature reaction; and then to the solution in the low temperature by adding sodium nitrite aqueous solution in the reaction; the end of the reaction the temperature of the reaction solution, adjusts pH value, then through steam distillation to obtain 2-bromo-6-methylpyridine; the cuprous cyanide and lithium bromide is added to the mass is 2-bromo-6-methylpyridine quality 2-5 times in DMF, after heating the solution, is added 2-bromo-6-methylpyridine, reaction of the; cooling the solution after the reaction, water, through the water vapor distillation to obtain the product. The security of operation of this method, low toxicity, high yield, is suitable for industrial production. (by machine translation)

Synthesis of nitriles from aldehydes with trimethylphenylammonium tribromide and ammonium acetate

Various aromatic and heterocyclic aldehydes were easily converted to respective nitriles with the combination of trimethylphenylammonium tribromide and ammonium acetate in good yields at room temperature.

Palladium(II)-catalyzed direct conversion of methyl arenes into aromatic nitriles

From methyl to nitrile: A mild ammoxidation method, which directly converts methyl arenes into aromatic nitriles, has been developed by using Pd(OAc) 2 and N-hydroxyphthalimide (NHPI) as the catalysts, and tert-butyl nitrite as the nitrogen source and oxidant. Copyright

AZABICYCLO [4.1.0] HEPT - 4 - YL DERIVATIVES AS HUMAN OREXIN RECEPTOR ANTAGONISTS

This invention relates to azabicyclo[4.1.0]hept-4-yl derivatives and their use as pharmaceuticals.

2 - (PYRIDIN- 2 -YL) -QUINAZOLINE DERIVATIVES AND THEIR USE AS MICROBICIDES

Compounds of formula I wherein the other substituents R1, R2, R3, R4, R5 and R6 are as defined in claim 1, and their use as microbicides.

Manganese oxide promoted liquid-phase aerobic oxidative amidation of methylarenes to monoamides using ammonia surrogates

In the presence of amorphous MnO2, various methylarenes (even with two or more methyl groups) could be selectively converted into the corresponding primary monoamides in moderate to high yields. The observed catalysis was truly heterogeneous, and the retrieved amorphous MnO2 catalyst could be reused without an appreciable loss of its catalytic performance. Copyright

Development of Pd/C-catalyzed cyanation of Aryl halides

A practical method for palladium-catalyzed cyanation of aryl halides using Pd/C is described. The new method can be applied to a variety of aryl bromide and active aryl chloride substrates to effect efficient conversions. The process features many advantages over existing cyanation conditions and the practical utility of the process has been demonstrated on scale.