694-85-9

Usage

Uses

Used in Pharmaceutical Industry:
1-Methyl-2-pyridone is used as a reactant in the trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis. This process is particularly important in the synthesis of pharmaceutical compounds, as trifluoromethylated molecules often exhibit enhanced biological activity and metabolic stability.
Used in Chemical Synthesis:
1-Methyl-2-pyridone is used as a versatile building block in the synthesis of various organic compounds. Its reactivity allows it to participate in a wide range of chemical reactions, making it a valuable intermediate in the production of pharmaceuticals, agrochemicals, and other specialty chemicals.
Chemical Properties:
1-Methyl-2-pyridone is a clear yellowish to brown-red liquid after melting. Its physical properties, such as solubility and boiling point, make it suitable for use in various chemical processes and reactions.

Synthesis Reference(s)

Journal of the American Chemical Society, 78, p. 416, 1956 DOI: 10.1021/ja01583a045The Journal of Organic Chemistry, 45, p. 4508, 1980 DOI: 10.1021/jo01310a052Tetrahedron Letters, 25, p. 1591, 1984 DOI: 10.1016/S0040-4039(01)90019-X

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

Upstream product

• 186581-53-3 diazomethane 
• 142-08-5 2-Pyridone 
• 110-86-1 pyridine 
• 80-48-8 methyl p-toluene sulfonate 
• 74-88-4 methyl iodide 
• 41681-14-5 1-Methyl-2-(methylthio)pyridinium iodide 
• 4088-63-5 1-methyl-2(1H)-pyridinimine 
• 2044-27-1 1-methyl-2-pyridinethione 
• 3847-19-6 2-acetoxypyridine 
• 121-69-7 N,N-dimethyl-aniline 
• 110-94-1 1,5-pentanedioic acid 
• 67367-26-4 2-methoxynicotinic acid methyl ester 
• 23353-96-0 pyridin-2(3H)-one 
• 353-39-9 Trimethylsulfonium Fluoride 

Downstream Products

• 109-09-1 2-chloropyridine 
• 51859-09-7 1-methyl-2-pyridone phenylimine 
• 51859-08-6 2-benzylidene-1-methyl-1,2-dihydro-pyridine 
• 16110-09-1 2,5 dichloropyridine 
• 931-20-4 1-methylpiperidin-2-one 
• 13131-19-6 (1R,8S)-9-Methyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2,4,6,11-tetraen-10-one 
• 13131-19-6 (1S,8R)-9-Methyl-9-aza-tricyclo[6.2.2.0^2,7]dodeca-2⁽⁷⁾,3,5,11-tetraen-10-one 
• 13131-19-6 2-methyl-5,6-benzo-2-azabicyclo<2.2.2>oct-7-ene-3-one 
• 86863-93-6 2-(Ethoxycarbonyl)-1-(trimethylsilyl)benzol 
• 121463-25-0 (1R,6R)-1,6-Bis-(2-chloro-phenyl)-1,6-diphenyl-hexa-2,4-diyne-1,6-diol; compound with 1-methyl-1H-pyridin-2-one 
• 91168-58-0 1,2-dihydro-2-(4-ethoxybenzoylcyanomethylidene)-1-methylpyridine 
• 121463-31-8 [(4R,5R)-5-(Hydroxy-diphenyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-diphenyl-methanol; compound with 1-methyl-1H-pyridin-2-one 
• 81971-39-3 5-bromo-1-methylpyridin-2(1H)-one 
• 81971-38-2 3-bromo-1-methyl-1H-pyridin-2-one 

Relevant academic research and scientific papers

Accelerated hydrolysis of α-halo and α-cyano pyridinium relative to uracil derivatives: A model for ODCase-catalyzed hydrolysis of 6-cyanoUMP

α-Halo and α-cyano pyridiniums were found to undergo facile hydrolysis, in contrast to the sluggish reactions of corresponding uracils. The greatly enhanced rates found with pyridinium compounds have indicated a possible source of the rate acceleration seen in the hydrolysis of 6-cyanouridine 5′-monophosphate catalyzed by orotidine 5′-monophosphate decarboxylase.

Micellar Effects upon the Reaction of Hydroxide Ion with N-Alkyl-2-bromopyridinium Ion

The reactivity of N-alkyl-2-bromopyridinium ions (alkyl = Me, Et, n-C12H25, n-C14H29, n-C16H33) toward OH(-) is affected by cationic micelles of alkyltrimethylammonium chloride or bromide (alkyl = n-C14H29, n-C16H33) which inhibit reactions of the methyl

PhICl2/NH4SCN-Mediated Oxidative Regioselective Thiocyanation of Pyridin-2(1H)-ones

The reaction of pyridin-2(1H)-ones with PhICl2 and NH4SCN enables an efficient regioselective thiocyanation, leading to the synthesis of the biologically interesting C5 thiocyanated 2-pyridones in good to high yields. The mechanistic pathway of this metal-free approach is postulated to involve the formation of the reactive thiocyanogen chloride from the reaction of PhICl2 and NH4SCN followed with the regioselective electrophilic thiocyanation of the pyridin-2(1H)-one ring.

Manganese-Promoted Regioselective Direct C3-Phosphinoylation of 2-Pyridones

A highly efficient and regioselective manganese-induced radical oxidative direct C?P bond formation between 2-pyridones and secondary phosphine oxides was developed. The C3-selective phosphinoylation was conveniently achieved through a combination of substoichiometric manganese and persulfate oxidant under mild conditions. Various 3-phosphinoylated pyridone products can be obtained in moderate to high yields. Preliminary mechanistic studies suggest that the reaction is likely to involve a radical pathway induced by catalytically active Mn3+ species.

Decarboxylation of orotic acid analogues: Comparison of solution and gas-phase reactivity

The decarboxylation of orotic acid and analogues have been investigated as a model for enzymatic decarboxylation catalyzed by orotidine-5′-monophosphate decarboxylase (ODCase). The rate of decarboxylation of 1-methyl-4-pyridone-2-carboxylic acid in solution has been reported to be three orders of magnitude greater than those of 1,3-dimethylorotic acid and 1-methyl-2-pyridone-6-carboxylic acid in solution. Here, the gas-phase decarboxylation of the three corresponding carboxylates were investigated. The carboxylate of 1,3-dimethylorotic acid decarboxylates at a faster rate and thus the relative rates of decarboxylation are different from those observed in solution. The relative rates of decarboxylation correlate well with the stability of the corresponding carbanions and the calculated activation energies for gas-phase decarboxylation. Therefore, the reactions in the gas phase seem to go through the direct decarboxylation mechanism whereas the reactions in solution likely go through zwitterionic intermediates as previously proposed.

Iron-Catalyzed Reactions of 2-Pyridone Derivatives: 1,6-Addition and Formal Ring Opening/Cross Coupling

In the presence of simple iron salts, 2-pyridone derivatives react with Grignard reagents under mild conditions to give the corresponding 1,6-addition products; if the reaction medium is supplemented with an aprotic dipolar cosolvent after the actual addition step, the intermediates primarily formed succumb to ring opening, giving rise to non-thermodynamic Z,E-configured dienoic acid amide derivatives which are difficult to make otherwise. Control experiments as well as the isolation and crystallographic characterization of a (tricarbonyl)iron pyridone complex suggest that the active iron catalyst generated in situ exhibits high affinity to the polarized diene system embedded into the heterocyclic ring system of the substrates, which likely serves as the actual recognition element.

Metal-free regioselective direct thiolation of 2-pyridones

A highly regioselective metal-free direct C-H thiolation of 2-pyridones with disulfides or thiols has been developed. A combination of persulfate and a commercially available halide source such as LiCl, NCS or I2 enables the successful direct incorporation of a sulfide moiety into the 5-position of pyridone under mild conditions, providing a useful and convenient approach for the preparation of a diverse array of 5-thio-substituted pyridones in moderate to excellent yields.

Catalytic O- to N-Alkyl Migratory Rearrangement: Transition Metal-Free Direct and Tandem Routes to N-Alkylated Pyridones and Benzothiazolones

The present study reports the synthesis of N-alkylated pyridones and benzothiazolones via O- to N-alkyl group migration under transition metal-free TfOH-catalyzed reaction conditions for the first time, to the best of our knowledge. Primary as well as secondary alkyl groups smoothly migrate under the present reaction conditions. Moreover, a minor modification of the protocol used in this study is found to be applicable for an entirely new tandem synthesis of 2-alkoxy-N-heterocycles from the simplest starting materials in a solvent-free reaction conditions. Density Functional Theory (DFT) calculation identifies the energy species associated with the rearrangement, whereas, mechanistic experiments explore the role of the catalyst as the alkyl group transfer mediator. (Figure presented.).

Synthetic method for drug intermediate N-methylpyridin-2-one

The invention discloses a synthetic method for the drug intermediate N-methylpyridin-2-one. The synthetic method comprises the following steps: adding 6-methoxypyridine, a potassium chloride solutionand a heptane solution into a reaction vessel, controlling a solution temperature, adding an aqueous solution and aluminum isopropoxide, controlling a stirring speed and continuing a reaction; and adding osmium trichloride powder, controlling the temperature, continuing the reaction, then lowering the temperature, carrying out stand so as to realize layering of the obtained solution, separating anoil layer, carrying out washing with a sodium sulfate solution a plurality of times, then carrying out washing with a xylene solution a plurality of times, carrying out recrystallization in a cyclohexene solution, and then carrying out dehydration with a dehydrating agent to obtain the finished N-methylpyridin-2-one.

Direct Pd(II)-Catalyzed Site-Selective C5-Arylation of 2-Pyridone Using Aryl Iodides

A straightforward Pd(II)-catalyzed general strategy was developed for the C5-selective arylation of the 2-pyridone core with easily available aryl iodides. The transformation was highly regioselective and accomplished with a wide scope and functional group tolerance. Silver nitrate played a crucial role in this direct site-selective arylation. The method was extended to synthesize biologically active molecules.