69003-17-4

Basic information

• Product Name: 1-Methyl-5,6-dihydropyridin-2(1H)-one
• Synonyms: 1-Methyl-5,6-dihydropyridin-2(1H)-one
• CAS NO: 69003-17-4
• Molecular Formula: C₆H₉NO
• Molecular Weight: 111.14176
• Mol File: 69003-17-4.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: 1-Methyl-5,6-dihydropyridin-2(1H)-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Methyl-5,6-dihydropyridin-2(1H)-one(69003-17-4)
• EPA Substance Registry System: 1-Methyl-5,6-dihydropyridin-2(1H)-one(69003-17-4)

Safety Data

• Hazardous Substances Data: 69003-17-4(Hazardous Substances Data)

Usage

Type of compound

Heterocyclic compound
Derived from pyridine

Usage

Precursor in the synthesis of various pharmaceuticals and agrochemicals

Physical appearance

Colorless, crystalline solid

Melting point

Around 89-92 °C

Solubility

Soluble in polar organic solvents such as ethanol and methanol

Chemical structure

Six-membered ring containing one nitrogen atom and one oxygen atom
With a methyl group attached to the nitrogen atom

Biological activity

Exhibits various biological activities

Interest

Of interest to medicinal chemists and pharmaceutical researchers for potential applications in drug discovery and development

Upstream product

• 626-67-5 N-methylcyclohexylamine 
• 931-20-4 1-methylpiperidin-2-one 
• 116461-13-3 1-methyl-3-phenacyl-2-piperidone 

Downstream Products

• 114980-40-4 N-methyl-4-phenyl-2-piperidinone 
• 358732-62-4 5-methyl-2,5,6,7-tetrahydro-pyrrolo[3,4-c]pyridin-4-one 

Relevant articles and documents

Transition-Metal-Free Multiple Functionalization of Piperidines to 4-Substituted and 3,4-Disubstituted 2-Piperidinones

Remote and multiple functionalization of piperidines without the use of transition-metal catalysts and elaborate directing groups is one of the major challenges in organic synthesis. Herein is reported an unprecedented two-step protocol that enables the multiple functionalization of piperidines to either 4-substituted or trans-3,4-disubstituted 2-piperidones. First, by exploiting the duality of TEMPO reactivity, which under oxidative and thermal conditions fluctuates between cationic and persistent-radical form, a novel multiple C(sp3)-H oxidation of piperidines to α,β-unsaturated 2-piperidones was developed. Second, the intrinsic low reactivity of the unsaturated piperidones toward conjugated Grignard additions was overcome by using trimethylsilyl chloride (TMSCl) as Lewis acid. Subsequently, conjugated Grignard addition/electrophilic trapping protocol provided substituted 2-piperidone intermediates, some of which were then transformed into pharmaceutical alkaloids.

Unprecedented copper-catalyzed asymmetric conjugate addition of organometallic reagents to α,β-unsaturated lactams

For the first time, an excellent enantioselectivity has been obtained in the conjugate addition of hard organometallic reagents to α,β-unsaturated lactams bearing appropriate protecting-activating groups on the nitrogen.

Inhibition of indoleamine-N-methyl transferase by 2-iminopyridines

A method of inhibiting indoleamine-N-methyl transferase comprises the administration to a host of a therapeutically effective amount of 1-alkyl-2-iminopyrrolidines or 1-alkyl-2-iminopyridines or pharmaceutically acceptable salts thereof.