6974-72-7

Usage

Uses

Used in Organic Synthesis:
Pyridine-2-carboxamide 1-oxide is used as a reagent in organic synthesis for its versatile chemical properties and ability to form various intermediates.
Used in Pharmaceutical Industry:
Pyridine-2-carboxamide 1-oxide is used as a precursor to various pharmaceutical compounds due to its unique structure and reactivity.
Used in Neuroprotection:
Pyridine-2-carboxamide 1-oxide is being studied for its potential use in the treatment of various neurodegenerative and inflammatory conditions, as it has been found to have protective effects on cells.
Used in Dye and Pigment Production:
Pyridine-2-carboxamide 1-oxide is used in the production of dyes, pigments, and other chemicals, leveraging its chemical properties for color development and stability.

InChI:InChI=1/C6H6N2O2/c7-6(9)5-3-1-2-4-8(5)10/h1-4H,(H2,7,9)

Upstream product

• 1452-77-3 pyridine-2-carboxylic acid amide 
• 38195-81-2 1-oxy-pyridine-2-carboxylic acid methyl ester 
• 1003-67-4 4-methylpyridine-1-oxide 
• 931-19-1 2-methylpyridine N-oxide 
• 24145-26-4 (Z)-2-pyridinecarbaldehyde 1-oxide oxime 
• 24145-28-6 (E)-2-pyridinecarbaldehyde 1-oxide oxime 

Downstream Products

• 14150-95-9 2-aminopyridine N-oxide 
• 2402-98-4 2-cyanopyridine N-oxide 
• 121779-80-4 C₂₇H₂₂N₆O₄S₂ 
• 1452-77-3 pyridine-2-carboxylic acid amide 

Relevant academic research and scientific papers

Oxidation of tertiary nitrogen compounds to N-oxides by molecular oxygen-aldehyde system in the absence of metal catalyst

A variety of tertiary nitrogen compounds have been oxidized to corresponding N-oxides in near quantitative yields by molecular oxygen/2-methylpropanal system in the absence of metal catalyst.

An efficient synthesis of heterocyclic N-oxides over molecular sieve catalyst

Heterocyclic N-oxides have been synthesized in very high yields over redox molecular sieve catalysts in the presence of H2O2.

ELUCIDATION OF THE REACTION PATH FOR THE NITROSATION OF 2- AND 4-METHYLPYRIDINE 1-OXIDES WITH ALKYL NITRITE IN LIQUID AMMONIA

The reaction path for the nitrosation of 2- and 4-methylpyridine 1-oxides with alkyl nitrite in the presence of NaNH2 in liquid NH3 was elucidated experimentally, and theoretically by the use of a semiempirical molecular orbital method (PM3 method).In the case of the nitrosation of 4-methylpyridine 1-oxide at room temperature, only 4-pyridinecarboxamide 1-oxide was obtained, while at -33 deg C a thermodynamically unstable aldoxime, (Z)-4-pyridinecarbaldehyde 1-oxide oxime, which was easily transformed into E-form by heating, was obtained.On the other hand, the nitrosation of 2-methylpyridine 1-oxide gave only a thermodynamically stable aldoxime, (E)-2-pyridinecarbaldehyde 1-oxide oxime, both at room temperature and at -33 deg C.These results were reasonably explained by PM3 method.

REINVESTIGATION OF NITROSATION OF METHYLPYRIDINES AND THEIR 1-OXIDES AND DEOXYGENATION OF 3-PYRIDINECARBALDEHYDE 1-OXIDE OXIME

Treatment of methylpyridines and their 1-oxides with t-butyl nitrite in the presence of potassium t-butoxide in liquid ammonia afforded the corresponding aldoximes in good yields except for the case of 3-methylpyridine.The reaction of 3-methylpyridine with t-butyl nitrite in the presence of lithium 2,2,6,6-tetramethylpiperidide and N,N,N',N'-tetramethylethylenediamine in tetrahydrofuran at -78 deg C led to 3-(3-methyl-4-pyridyl)methylpyridine.Deoxygenation of 3-pyridinecarbaldehyde 1-oxide oxime was effected in 78percent yieldby the action of t-butyldimethylsilyl chloride-imidazolesodium iodide-zinc followed by desilylation with tetrabutylammonium fluoride to give 3-pyridinecarbaldehyde oxime.