38557-82-3

Usage

Uses

Used in Organic Synthesis:
Isonicotinamide 1-oxide is used as a synthetic building block for the creation of a wide range of organic compounds. Its unique chemical structure allows it to be a versatile component in the synthesis of various molecules, including pharmaceuticals, agrochemicals, and other specialty chemicals.
Used in Pharmaceutical Industry:
Isonicotinamide 1-oxide is used as a key intermediate in the development of new drugs, particularly in the synthesis of antitubercular and antimicrobial agents. Its incorporation into drug molecules can enhance their efficacy and selectivity, making it a valuable asset in the pharmaceutical industry.
Used in Chemical Research:
In the field of chemical research, Isonicotinamide 1-oxide serves as a valuable compound for studying reaction mechanisms, exploring new synthetic routes, and understanding the properties of various chemical classes. Its reactivity and structural features make it an attractive candidate for research and development efforts.

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

Upstream product

• 14906-37-7 ethyl isonicotinate N-oxide 
• 1453-82-3 isonicotinamide 
• 1003-67-4 4-methylpyridine-1-oxide 
• 100-48-1 pyridine-4-carbonitrile 
• 24145-27-5 (Z)-(1-oxidopyridin-1-ium-4-yl)-4-carbaldoxime 
• 24145-29-7 (E)-4-pyridinecarbaldehyde 1-oxide oxime 
• 91-66-7 N,N-diethylaniline 
• 1570-45-2 isonicotinic acid ethylester 
• 14906-59-3 4-cyanopyridine N-oxide 

Downstream Products

• 14906-59-3 4-cyanopyridine N-oxide 
• 33252-30-1 2-chloro-4-pyridinenitrile 
• 125230-39-9 1-(4-Chloro-phenyl)-3-(1-oxy-pyridine-4-carbonyl)-urea 
• 121779-83-7 C₂₇H₂₂N₆O₄S₂ 
• 121779-89-3 1-Oxy-N-[3-phenyl-thiazolidin-(2Z)-ylidene]-isonicotinamide 
• 3731-53-1 4-(aminomethyl)pyridine 
• 1453-82-3 isonicotinamide 
• 91447-89-1 2-chloropyridine-4-carbothioamide 
• 63919-16-4 Thioisonicotinamid-1-oxid 
• 1279114-11-2 C₆H₆N₂O₂*C₁₂H₁₁ClN₂O₅S 

Relevant academic research and scientific papers

Organic synthesis via magnetic attraction: Benign and sustainable protocols using magnetic nanoferrites

Magnetic nano-catalysts have been prepared using simple modification of iron ferrites. The nm size range of these particles facilitates the catalysis process, as an increased surface area is available for the reaction; the easy separation of the catalysts by an external magnet and their recovery and reuse are additional beneficial attributes. Glutathione bearing nano-ferrites have been used as organocatalysts for the Paal-Knorr reaction and homocoupling of boronic acids. Nanoferrites, post-synthetically modified by ligands, were used to immobilize nanometals (Cu, Pd, Ru, etc.) which enabled the development of efficient, sustainable and green procedures for azide-alkynes-cycloaddition (AAC) reactions, C-S coupling, O-allylation of phenol, Heck-type reactions and hydration of nitriles.

Comparative rate study on the oxidation of nicotinamide and isonicotinamide by permanganate in acidic medium

A comparative rate study on the oxidation of nicotinamide and isonicotinamide by potassium permanganate has been carried out in acidic solutions over an extended [H+]·range (1 × 10 -5-1.0 mol L-1). Under the similar reaction conditions, the oxidation of pyridine is imperceptible. Further, In the absence of acid none of the two amides is oxidised and in both cases, the N-protonated amide species appears to be reactive. For nicotinamide, the results are in agreement with the two-term rate law (A). The oxidation product was corresponding N oxide. -d[MnO4 -Ydt = (k0K + k1KK 1 [H+]) [S]0, [MnO4 -]t [H+Y(1 + K [H+)]) (A) On the other hand, the oxidation of isonicotinamide follows a simpler rate law (B). -d[MnO4-Ydt = k0K [S]0 [MnO 4-]1 [H+Y(1 + K. [H+]) (B) The values of k0, K. and k1K1 for nicotinamide were round to be 5.5 × 10-3 L. mol-1 s-1, 1.8 × 104 and 1.0 × 10-2 L. mol-1 s-1, respectively at 35 °C. And for isonicotinamide, the k0, and K. values were 4.4 × 10 -3 L. mol-1 s-1 and 5.6 × 103 respectively at 35 °C. The oxidation of nicotinamide is faster than the oxidation of isonicotinamide. It appears that the presence of -CONH2 group at position 3 activates the ring nitrogen more for oxidation than the presence of this group at position 4.

FUROISOQUINOLINE DERIVATIVES, PROCESS FOR PRODUCING THE SAME AND USE THEREOF

A compound having a partial structure represented by Formula: or a salt thereof has an excellent phosphodiesterase (PDE) IV-inhibiting effect, and is useful as a prophylactic or therapeutic agent against inflammatory diseases, for example, bronchial asthma, chronic obstructive pulmonary disease (COPD), rheumatoid arthritis, autoimmune disease, diabetes and the like.

An Excellent Method for the Mild and Safe Oxidation of N-Heteroaromatic Compounds and Tertiary Amines

Selective, mild and safe N-oxidation of N-heteroaromatic compounds and tertiary amines affording high product yields was achieved by using the H2O2-urea/phthalic anhydride system. Key Words: N-Oxidation / Hydrogen peroxide / Urea / Phthalic anhydride

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.