4,4-dimethyl-2-pyrrolidinone Chemical Properties

Melting point:

38-40°

Boiling point:

150-155℃ (18 Torr)

Density 

0.945±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Room Temperature

pka

16.70±0.40(Predicted)

form 

Solid

color 

White to cream

Water Solubility 

Sparingly soluble in water.(0.26 g/L) (25°C),

Sensitive 

Air Sensitive

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

4,4-dimethyl-2-pyrrolidinone Usage And Synthesis

Uses

It is used as pharmaceutical intermediate. Benzoylthiophenes are allosteric enhancers (AE) of agonist activity at the A1 adenosine receptor.

Synthesis

The general procedure for the synthesis of 4,4-dimethyl-2-pyrrolidinone from ethyl 3,3-dimethyl-4-nitrobutanoate was as follows: ethyl 3,3-dimethyl-4-nitrobutanoate (22.65 g, 119.8 mmol) was dissolved in methanol (120 ml), followed by the addition of 10% palladium/activated carbon catalyst (250 mg). The reaction mixture was transferred to a hydrogenation unit (Parr Instrument Company), operated under evacuation and the reaction mixture was stirred at 110 °C. The reaction mixture was subjected to five hydrogenation operations with hydrogen (4.4 atmospheres) over a period of 16 hours. Upon completion of the reaction, the reaction mixture was filtered, the catalyst was washed with methanol, and the solvent was subsequently removed by evaporation to afford the oily product 4,4-dimethyl-2-pyrrolidinone (13.14 g, 97% yield).

References

[1] Patent: US2008/39456, 2008, A1. Location in patent: Page/Page column 44

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