77015-41-9

Basic information

• Product Name: 1-propanoylpyrrolidin-2-one
• Synonyms: 1-propanoylpyrrolidin-2-one
• CAS NO: 77015-41-9
• Molecular Formula: C7H11NO2
• Molecular Weight: 141.17
• Mol File: 77015-41-9.mol
• Article Data: 5

Chemical Properties

• Boiling Point: 257.9 °C at 760 mmHg
• Flash Point: 114.5 °C
• Appearance: /
• Density: 1.138 g/cm³
• Vapor Pressure: 0.0142mmHg at 25°C
• Refractive Index: 1.491
• CAS DataBase Reference: 1-propanoylpyrrolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 1-propanoylpyrrolidin-2-one(77015-41-9)
• EPA Substance Registry System: 1-propanoylpyrrolidin-2-one(77015-41-9)

Safety Data

• Hazardous Substances Data: 77015-41-9(Hazardous Substances Data)

Usage

General Description

1-Propanoylpyrrolidin-2-one, also known as PVP K-30, is a chemical compound commonly used as a pharmaceutical excipient, particularly in the formulation of solid oral dosage forms. It belongs to the class of pyrrolidones and is often used as a binder, stabilizer, and disintegrant in tablets and capsules. PVP K-30 has excellent solubility in water and organic solvents, and it is non-irritating and non-toxic, making it suitable for use in pharmaceutical applications. It also has film-forming properties, making it useful in the production of coatings for tablets. Due to its versatile properties, PVP K-30 is widely used in the pharmaceutical industry for formulating various drug products.

InChI:InChI=1/C7H11NO2/c1-2-6(9)8-5-3-4-7(8)10/h2-5H2,1H3

Upstream product

• 616-45-5 2-pyrrolidinon 
• 79-03-8 propionyl chloride 
• 4553-05-3 1-pyrrolidin-1-yl-propan-1-one 
• 71-23-8 propan-1-ol 
• 123-62-6 propionic acid anhydride 

Downstream Products

• 1192-29-6 2-ethyl-1-pyrroline 

Relevant articles and documents

CuCl/TMEDA/nor-AZADO-catalyzed aerobic oxidative acylation of amides with alcohols to produce imides

Although aerobic oxidative acylation of amides with alcohols would be a good complement to classical synthetic methods for imides (e.g., acylation of amides with activated forms of carboxylic acids), to date, there have been no reports on oxidative acylation to produce imides. In this study, we successfully developed, for the first time, an efficient method for the synthesis of imides through aerobic oxidative acylation of amides with alcohols by employing a CuCl/TMEDA/nor-AZADO catalyst system (TMEDA = teramethylethylendiamine; nor-AZADO = 9-azanoradamantane N-oxyl). The proposed acylation proceeds through the following sequential reactions: aerobic oxidation of alcohols to aldehydes, nucleophilic addition of amides to the aldehydes to form hemiamidal intermediates, and aerobic oxidation of the hemiamidal intermediates to give the corresponding imides. This catalytic system utilizes O2 as the terminal oxidant and produces water as the sole by-product. An important point for realizing this efficient acylation system is the utilization of a TMEDA ligand, which, to the best of our knowledge, has not been employed in previously reported Cu/ligand/N-oxyl systems. Based on experimental evidence, we consider that plausible roles of TMEDA involve the promotion of both hemiamidal oxidation and regeneration of an active CuII-OH species from a CuI species. Here promotion of hemiamidal oxidation is particularly important. Employing the proposed system, various types of structurally diverse imides could be synthesized from various combinations of alcohols and amides, and gram-scale acylation was also successful. In addition, the proposed system was further applicable to the synthesis of α-ketocarbonyl compounds (i.e., α-ketoimides, α-ketoamides, and α-ketoesters) from 1,2-diols and nucleophiles (i.e., amides, amines, and alcohols).

Synthesis and anticonvulsant activity of 1-acyl-2-pyrrolidinone derivatives

Several 1-acyl-2-pyrrolidinone derivatives were synthesized as derivatives of γ-aminobutyric acid (GABA), and their pharmacological activities and stabilities were investigated. The derivatives showed anticonvulsant effect on picrotoxin-induced seizure at a dose of 200 mg/kg. In particular, 1-decanoyl-2-pyrrolidinone (7) and 1-dodecanoyl-2-pyrrolidinone (8) had a high activity. The anticonvulsant activity showed a dose dependency. Some of 1-acyl-2-pyrrolidinone derivatives prolonged sleeping time which was induced by sodium pentobarbital and showed a recovery from disruption of the memory of passive avoidance response, which was induced by an electroconvulsive shock. As shown by the results of the stability study of 1-acetyl-2-pyrrolidinone (1), it was degraded in an acidic buffer and an alkaline buffer although 2-pyrrolidinone was stable. 1-Acyl-2-pyrrolidinone derivatives were degraded in liver and brain homogenates of mouse and rat. They showed a degradation rate in rat plasma. Conversion of 8 to GABA in mouse liver homogenate was demonstrated. These results suggested that the pharmacological activity of 1-acyl-2-pyrrolidinone is probably due to the release of GABA by hydrolysis of derivatives although further work is necessary.

Photocatalytic Oxidations of Lactams and N-Acylamines

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