5220-65-5

Basic information

• Product Name: 5-ACETYL-6-METHYL-2(1H)-PYRIDINONE
• Synonyms: 5-ACETYL-6-METHYL-2(1H)-PYRIDINONE
• CAS NO: 5220-65-5
• Molecular Formula: C8H9NO2
• Molecular Weight: 151.16
• Mol File: 5220-65-5.mol

Chemical Properties

• Melting Point: 203-205°
• Boiling Point: 349.7°Cat760mmHg
• Flash Point: 168.5°C
• Appearance: /
• Density: 1.138g/cm³
• Vapor Pressure: 4.62E-05mmHg at 25°C
• Refractive Index: 1.508
• CAS DataBase Reference: 5-ACETYL-6-METHYL-2(1H)-PYRIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: 5-ACETYL-6-METHYL-2(1H)-PYRIDINONE(5220-65-5)
• EPA Substance Registry System: 5-ACETYL-6-METHYL-2(1H)-PYRIDINONE(5220-65-5)

Safety Data

• HazardClass: IRRITANT
• Hazardous Substances Data: 5220-65-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
5-ACETYL-6-METHYL-2(1H)-PYRIDINONE is used as an inotropic agent for improving the contractile force of the heart muscle. This application is particularly relevant for patients with heart failure or other conditions that affect the heart's ability to pump blood effectively.

InChI:InChI=1/C8H9NO2/c1-5-7(6(2)10)3-4-8(11)9-5/h3-4H,1-2H3,(H,9,11)

Upstream product

• 13729-69-6 5-acetyl-6-methyl-1,2,3,4-tetrahydro-2-pyridinone 
• 123-54-6 acetylacetone 
• 52600-60-9 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridine-carboxamide 
• 18856-72-9 3-dimethylaminomethylenepentane-2,4-dione 
• 33884-41-2 ethoxylideneacetylacetone 
• 52600-53-0 5-acetyl-1,2-dihydro-6-methyl-2-oxonicotinonitrile 
• 80012-14-2 (E)-4-amino-pent-3-en-2-one 
• 1118-66-7 4-amino-3-penten-2-one 
• 922-67-8 propynoic acid methyl ester 
• 88302-06-1 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarboxylic acid 

Downstream Products

• 88877-00-3 5-acetyl-6-(2-dimethylaminoethenyl)-2(1H)-pyridinone 
• 140692-93-9 2-chloro-5-methyl-1,6-naphthyridine 
• 1085267-10-2 1-[2-(4-benzylpiperidin-1-yl)ethyl]-3-(5-methyl[1,6]naphthyridin-2-yl)urea 
• 1085267-03-3 2-(4-benzylpiperidin-1-yl)-N-(5-methyl[1,6]naphthyridin-2-yl)acetamide 
• 1085266-43-8 [2-(4-benzylpiperidin-1-yl)ethyl]-(5-methyl[1,6]naphthyridin-2-yl)amine 
• 147293-24-1 5-acetyl-3-bromo-6-<2-(dimethylamino)ethenyl>pyridin-2(1H)-one 
• 147293-25-2 3-bromo-5-methyl-1,6-naphthyridin-2(1H)-one 
• 136117-46-9 5-acetyl-3-bromo-6-methyl-2(1H)-pyridinone 
• 58405-00-8 5-acetyl-3-chloro-6-methyl-2(1H)-pyridinone 

Relevant articles and documents

UROTENSIN II RECEPTOR ANTAGONISTS

Compounds of the formula (I) wherein R1, R2, R3, R4, R5, R6, W, and Y are as described herein, or a tautomer, prodrug, solvate, or salt thereof. These compounds are useful as inhibitors of Urotensin II and are thus useful for treating a variety of disease

3-Hydroxypyrroles and 1H-Pyrrol-3(2H)-ones. Part 13. Reactions of Methoxymethylene Meldrum's Acids with 3-Hydroxypyrroles, with 3-Methoxypyrroles and with other Active Substrates, and Pyrolytic Heterocyclizations of the Products

Methoxymethylene Meldrum's acid 2 in acetonitrile solution acts a useful C-electrophile for active substrates such as pyrrole, indole or tertiary enaminones to give substitution products (e.g. 5, 6 or 12, respectively).Primary enaminones react exlusively at the nitrogen atom under these conditions.The effect of the ring substituents on the regiochemistry of electrophilic substitution of 3-hydroxypyrroles and 3-methoxypyrroles was studied using methoxymethylene Meldrum's acid as the electrophile.Flash vacuum pyrolysis of the Meldrum's acid derivatives obtained in many of these reactions gave access to a range of heterocyclic systems, including the pyridone 48, quinolinedione 43, benzazepinedione 41 and fused pyrones 50, 52 and 54.

Imidazo[1,2-a]pyridines. Synthesis and inotropic activity of new 5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinone derivatives

A series of 1,2-dihydro-5-imidazo[1,2-a]pyridinyl-2(1H)-pyridinones was synthesized and evaluated for positive inotropic activity. 1,2-Dihydro-5-imidazo[1,2-a]pyridin-6-yl-6-methyl-2-oxo-3- pyridinecarbonitrile (11a) hydrochloride monohydrate (E-1020) was found to be a potent and selective inhibitor of phosphodiesterase III and a long-acting, potent, orally active positive inotropic agent. Additional imidazo[1,2-a]pyridin-2-yl (3a), -3-yl (16), -7-yl (20) and -8-yl (24a) compounds were also prepared. Altering the pyridine substitution from the 2-position to the 6-position produced a 2-fold increase in the i.v. cardiotonic potency (ED50) from 52 to 23 μg/kg, while substitution at the 3-, 7- or 8-position reduced potency. In the 2-positional isomers, introduction of halogen groups enhanced the activity and 3-chloro-1,2-dihydro-5-(6-fluoroimidazo[1,2-a]pyridin-2-yl)-6-methyl-2(1H)- pyridinone (3a) was the most potent (i.v. ED50 11 μg/kg) in this seris. E-1020 is presently under development for the treatment of congestive heart failure.

A Facile and Novel Synthesis of 1,6-Naphthyridin-2(1H)-ones

A new and convenient procedure for the synthesis of 1,6-naphthyridin-2(1H)-ones and their derivatives is described.In the first scheme 5-acetyl-6--1,2-dihydro-2-oxo-3-pyridinecarbonitrile (4) obtained by the reaction of N,N-dimet

Novel alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones

This invention relates to alkoxyimino ether derivatives of 5-acyl-2(1H)-pyridinones and to their use as cardiotonic agents useful in treating cardiac failure, and to the process useful in the preparation thereof.

5-Acyl-2-(1H)-pyridinones

Novel 5-acyl-2-(1H)pyridinones and their use as cardiotonic agents. Typical of the compounds is 5-acetyl-1,2-dihydro-6-methyl-2-oxo-3-pyridinecarbonitrile which is prepared by condensing anionic cyano acetamide with 3-[(dimethylamino)methylenyl]-2,4-penta

5-Alkyl-1,6-naphthyridin-2(1H)-ones and cardiotonic use thereof

1-R"-3-Q-4-R'-5-R-1,6-naphthyridin-2(1H)-ones (I) or salts thereof, where R is lower-alkyl, R' is hydrogen or methyl, R" is hydrogen or lower-alkyl, and Q is hydrogen, hydroxy, amino, cyano, carbamyl, carboxy or aminocarbamyl, are useful as cardiotonic ag

5-Alkanoyl-6-alkyl-2(1H)-pyridinones, their preparation and their cardiotonic use

4-R2 -5-(Lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones (I), useful as cardiotonics, where R2 is hydrogen or methyl, are prepared by reacting 2-(lower-alkanoyl)-1-(lower-alkyl)ethenamine (II) with lower-alkyl 2-propynoate or 2-butynoate respectively or by hydrolyzing 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinonitrile (III), Q is CN) or corresponding 4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinamide to produce the corresponding 5-(lower-alkanoyl)-6-(lower-alkyl)-1,2-dihydro-2-oxonicotinic acid and decarboxylating said substituted nictotinic acid to produce I. Also disclosed and claimed are cardiotonic uses of 3-Q-4-R2 -5-(lower-alkanoyl)-6-(lower-alkyl)-2(1H)-pyridinones where Q is hydrogen or cyano and R2 is hydrogen or methyl (III). Also shown and claimed is methyl 4-acetyl-5-amino-2,4-hexadienoate or acid-addition salt thereof, useful as intermediate or cardiotonic.

5-(Hydroxyalkyl or alkanoyloxymethyl)-1,6-naphthyridin-2(1H)-one and cardiotonic use thereof

4-R'-5-Q-1,6-naphthyridin-2(1H)-ones (I), where R' is hydrogen or methyl and Q is hydroxymethyl, 1-hydroxyethyl alkanoyloxymethyl or 1-alkanoyloxyethyl, are produced by first reacting 4-R'-5-acetyl(or n-propanoyl)-6-[2-(di-lower-alkylamino]-2(1H)-pyridinone [III] with hydroxylamine or salt thereof to produce 4-R'-5-Q'-1,6-naphthyridin-2(1H)-one-6-oxide (II), where R' is defined as above and Q' is methyl or ethyl; next reacting II with an alkanoic anhydride to produce I where Q is alkanoyloxymethyl or 1-alkanoyloxyethyl; and, then hydrolyzing said alkanoyloxymethyl or -ethyl compound to produce I where Q is hydroxymethyl or 1-hydroxyethyl. Also shown is the cardiotonic use of II and I where Q is hydroxymethyl, 1-hydroxyethyl or alkanoyloxymethyl.

Reaction of 2-Dimethylaminomethylene-1,3-diones with Dinucleophiles.V. Synthesis of 5-Acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles and 1,2,5,6,7,8-Hexahydro-2,5-dioxo-3-quinolinecarboxamides

The reaction of open-chain sym-2-dimethylaminomethylene-1,3-diones Ia-d with sodium cyanoacetamide gave, generally in good yields, 6-substituted 5-acyl-1,2-dihydro-2-oxo-3-pyridinecarbonitriles IIa-d, whereas cyclohexane sym-2-dimethylaminomethylene-1,3-diones Ie-h afforded in general a mixture of 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarbonitriles and 5,6,7,8-tetrahydro-2,5-dioxo-2H-1-benzopyran-3-carboxamides, the latter being isolated in two cases.The reaction of Ie-h with cyanoacetamide in refluxing anhydrous ethanol gave 1,2,5,6,7,8-hexahydro-2,5-dioxo-3-quinolinecarboxamides IIIe-h in excellent yields, whereas Ia-d did not react with the exception of Ia which afforded in good yield 3-pyridinecarboxamide IIIa.Other 3-pyridinecarboxamides were obtained by partial hydrolysis of nitriles IIb,d. 3-Pyridine and 3-quinoline carboxamides were hydrolyzed in satisfactory yields with hydrochloric acid to the corresponding carboxylic acids, which were decarboxylated in good yields to 5-acyl-2(1H)-pyridinones and 7,8-dihydro-2,5-(1H,6H)-quinolinediones, respectively, by reflux in quinoline containing a catalytic amount of copper powder.