3-Cyano-6-methyl-2(1H)-pyridinone

3-Cyano-6-methyl-2(1H)-pyridinone Property

Melting point:

293-295 °C (lit.)

Boiling point:

247.23°C (rough estimate)

Density 

1.2296 (rough estimate)

refractive index 

1.5880 (estimate)

storage temp. 

Inert atmosphere,Room Temperature

solubility 

DMSO (Slightly), Methanol (Slightly)

form 

Solid

pka

9.03±0.10(Predicted)

color 

White to Pale Yellow

Water Solubility 

2.38 g/L (20 ºC)

BRN 

120412

InChI

InChI=1S/C7H6N2O/c1-5-2-3-6(4-8)7(10)9-5/h2-3H,1H3,(H,9,10)

InChIKey

FIMGYEKEYXUTGD-UHFFFAOYSA-N

SMILES

C1(=O)NC(C)=CC=C1C#N

CAS DataBase Reference

4241-27-4(CAS DataBase Reference)

EPA Substance Registry System

3-Pyridinecarbonitrile, 1,2-dihydro-6-methyl-2-oxo- (4241-27-4)

Safety

Hazard Codes 

Xn,Xi

Risk Statements 

36/37/38-20/21/22

Safety Statements 

36/37/39-26-22-36

RIDADR 

3276

WGK Germany 

3

TSCA 

Yes

HazardClass 

IRRITANT

PackingGroup 

III

HS Code 

2933399990

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H301Toxic if swalloed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

P501Dispose of contents/container to..…

3-Cyano-6-methyl-2(1H)-pyridinone Chemical Properties,Usage,Production

Chemical Properties

SLIGHTLY YELLOW GRANULAR CRYSTALLINE POWDER

Uses

3-Cyano-6-methyl-2(1H)-pyridinone is a reactant used in the synthesis of Milrinone (M344680), a selective phosphodiesterase inhibitor with vasodilating and positive inotropic activity. 3-It has also been used in the preparation of the N3?-pyridyl thiamine, a potent in vitro thiamine antagonist.

General Description

Supramolecular structures of coordination copper(I) compounds of 3-cyano-6-methyl-2(1H)-pyridinone has been investigated.

Synthesis

A 950 ml solution of tetrahydrofuran (THF) with 46.5 g of sodium methanolate was added to the reaction vessel and cooled in an ice bath to an internal temperature of 0 to 5°C. Subsequently, a mixed solution of 46.5 g of acetone and 59.6 g of ethyl formate was slowly added with a controlled drip time of 1 hour. After the dropwise addition, the ice bath was removed and the reaction system was allowed to slowly warm up to room temperature within 1 hour. Afterwards, the reaction solution was concentrated under reduced pressure (temperature not exceeding 50°C). The concentrate was transferred to another reaction vessel, 400 ml of aqueous solution of 67 g of cyanoacetamide and an appropriate amount of piperidine acetic acid (as a condensation catalyst) were added, and the reaction was refluxed for 2 hours. Upon completion of the reaction, the reaction was cooled to room temperature and the pH was adjusted with acetic acid to about 5. The reaction mixture was allowed to stand at room temperature overnight and subsequently cooled in an ice bath for 45 minutes for filtration. The filter cake was washed three times with ice water and finally dried under vacuum at 80 °C overnight to afford 65.5 g of the target compound 3-cyano-6-methyl-pyridone (61.0% yield) as a yellow solid.

References

[1] Patent: CN105037261, 2017, B. Location in patent: Paragraph 0048-0049
[2] Molecules, 2018, vol. 23, # 7,
[3] Patent: US6342504, 2002, B1. Location in patent: Page column 50
[4] Journal of Medicinal Chemistry, 1994, vol. 37, # 20, p. 3303 - 3312
[5] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 6, p. 2212 - 2215