3279-76-3

Usage

Uses

Used in Chemical Synthesis:
2-Hydroxy-6-methylpyridine is used as a reagent in the chemical synthesis industry for the formation of various compounds. Its ability to react with carboxylic acids makes it a valuable component in the creation of new molecules with potential applications in different fields.
Used in Pharmaceutical Research:
In the pharmaceutical industry, 2-Hydroxy-6-methylpyridine is used as a starting material for the development of new drugs. Its unique chemical properties allow it to be a key component in the synthesis of various medicinal compounds, potentially leading to the discovery of novel therapeutic agents.
Used in Material Science:
2-Hydroxy-6-methylpyridine can be utilized in the field of material science as a component in the development of new materials with specific properties. Its reactivity with carboxylic acids can be exploited to create materials with tailored characteristics for various applications, such as in electronics, coatings, or adhesives.
Used in Analytical Chemistry:
As a white to cream-colored crystalline powder, 2-Hydroxy-6-methylpyridine can be employed in analytical chemistry for the identification and quantification of specific compounds. Its distinct chemical properties make it a useful reference material or standard in various analytical techniques, such as chromatography or spectroscopy.

Synthesis Reference(s)

Journal of the American Chemical Society, 71, p. 1186, 1949 DOI: 10.1021/ja01172a014

InChI:InChI=1/C6H7NO/c1-5-3-2-4-6(8)7-5/h2-4H,1H3,(H,7,8)

Upstream product

• 109-06-8 α-picoline 
• 4775-98-8 δ-caprolactam 
• 1824-81-3 2-Amino-6-methylpyridine 
• 18368-63-3 6-chloro-2-picoline 
• 66909-37-3 6-hydroxy-2-methyl-nicotinic acid 
• 854389-41-6 2-hydroxy-6-methyl-pyridine-3,5-dicarboxylic acid 
• 63071-03-4 2-methoxy-6-methyl-pyridine 
• 128702-09-0 1-Benzyloxy-6-methyl-2-pyridone 
• 3424-43-9 ethyl 6-hydroxy-2-methylnicotinate 
• 31163-12-9 ethyl 6-chloro-2-methylnicotinate 
• 4027-39-8 2-methyl-6-oxo-1,4,5,6-tetrahydro-pyridine-3-carboxylic acid ethyl ester 
• 407-22-7 2-fluoro-6-methylpyridine 
• 18617-77-1 6-methyl-2-ethoxypyridine 
• 92138-20-0 natural Huperzine A 

Downstream Products

• 18368-63-3 6-chloro-2-picoline 
• 5315-25-3 2-bromo-6-methylpyridine 
• 3430-15-7 2,3,5-tribromo-6-methyl-pyridine 
• 22109-55-3 3,5-Dichlor-6-methyl-pyridin-2-ol 
• 39745-39-6 6-methyl-3-nitrohydropyridin-2-one 
• 63071-03-4 2-methoxy-6-methyl-pyridine 
• 91012-57-6 (6-methyl-[2]pyridyloxy)-acetic acid ethyl ester 
• 319916-42-2 3-methyl-2-(6-methyl-pyridin-2-yloxy)-cyclohex-2-enone 
• 319916-44-4 3,5,5-trimethyl-2-(6-methyl-pyridin-2-yloxy)-cyclohex-2-enone 
• 319916-43-3 5,5-dimethyl-2-(6-methyl-pyridin-2-yloxy)-cyclohex-2-enone 
• 319916-45-5 6-tert-butyl-3-methyl-2-(6-methyl-pyridin-2-yloxy)-cyclohex-2-enone 
• 54923-31-8 5-bromo-2-hydroxy-6-methylpyridine 
• 500587-45-1 3,5-dibromo-2-hydroxy-6-methylpyridine 
• 374633-33-7 3-bromo-2-hydroxy-6-methylpyridine 

Relevant academic research and scientific papers

Rhodium(III)-Catalyzed Site-Selective C-H Alkylation and Arylation of Pyridones Using Organoboron Reagents

In this study we developed a method for the pyridine-directed, rhodium-catalyzed, site-selective C-H alkylation and arylation of pyridones using commercially available trifluoroborate reagents. This simple and versatile transformation proceeded smoothly under relatively mild conditions with perfect site selectivity. The coupling groups in the boron reagents can be extended to primary alkyl, benzyl, and cycloalkyl. Moreover, direct C-H arylation products could also be obtained under similar conditions.

Controlled oxygen release from pyridone endoperoxides promotes cell survival under anoxic conditions

In tissue engineering, survival of larger constructs remains challenging due to limited supply of oxygen caused by a lack of early vascularization. Controlled release of oxygen from small organic molecules represents a possible strategy to prevent cell death under anoxic conditions. A comprehensive study of methylated pyridone-derived endoperoxides has led to the development of water-soluble molecules that undergo retro-Diels-Alder reactions in aqueous environment releasing oxygen in high yield and with half-lives of up to 13 h. These molecules in combination with vitamin C as singlet oxygen quencher significantly improved survival of 3T3 fibroblasts and rat smooth muscle cells challenged with oxygen-depleted conditions.

Rh(I)-Catalyzed C6-Selective Decarbonylative Alkylation of 2-Pyridones with Alkyl Carboxylic Acids and Anhydrides

A Rh-catalyzed chelation-assisted C6-selective C-H activation/alkylation of 2-pyridones with readily available alkyl carboxylic acids or anhydrides is introduced. The reaction proceeds via substrate decarbonylation. This approach merges C-H functionalization with readily available anhydrides, allowing for the efficient synthesis of various C6-alkylated 2-pyridones with good functional group tolerance.

Asymmetric Homogeneous Hydrogenation of 2-Pyridones

An asymmetric homogeneous hydrogenation of 2(1H)-pyridones has been developed, using a ruthenium complex bearing two chiral N-heterocyclic carbene (NHC) ligands. To the best of our knowledge, the presented reaction is the first example of a homogeneous asymmetric conversion of 2-pyridones into the corresponding enantioenriched 2-piperidones.

Demethylation of methoxypyridines with sodium trimethylsilanethiolate

Demethylation of methoxypyridines was accomplished in 55-87percent yield by use of ca. 1.5-2.5 equivalents of NaSSiMe3 in 1,3-dimethyl-2-imidazolidinone at 120-180 deg C.This method was found applicable to a methoxyquinoline and methoxypyridines containing a second substituent, such as Cl, OMe, and COOMe.

The Photolysis of 1-Benzyloxy-2-pyridone and its Methyl Derivatives. Correlation with 1H NMR-derived Ground-state Conformation

In addition to methyl substituent effects on the reactivities of the vibrationally unrelaxed excited singlet state of 1-benzyloxy-2-pyridone (1), deuterium isotope effects on the reaction efficiencies of (1) and its methyl derivatives are discussed on the basis of their major ground-state conformations, as analysed by 1H NMR spectroscopy.It is suggested that intramolecular hydrogen abstraction of the benzylic hydrogen by the amido carbonyl oxygen in (1) competes with N-O bond cleavage in polar solvents.Effects exerted by both a methyl group and a non-polar solvent aremanifested by the predominant N-O bond cleavage in the vibrationally 'hot' excited singlet state.

The structures of huperzine A and B, two new alkaloids exhibiting marked anticholinesterase activity

Huperzine A and B, two new Lycopodium alkaloids isolated from Huperzia serrata (Thunb.) Trev., are shown to possess structures 1 and 3, respectively, on the basis of chemical and spectroscopic data.

Nucleophilic Displacement of N-Aryl and Heteroaryl Groups. Part 5. Conversion of 2-Aminopyridines into 2-Pyridones

2-Ethoxycarbonyl-1-(2-pyridyl)pyridinium cations (3) (easily prepared from 2-aminopyridine and the appropriate pyrylium salt) are converted by dilute NaOH at 25 deg C into 1-(substituted 2-pyridylcarbonyl)-2-pyridones (7).Compounds (7) are readily hydrolysed to 2-pyridones.