3-OXO-3-(3-PYRIDINYL)PROPANENITRILE Chemical Properties

Melting point:

79-81°C

Boiling point:

344.3±22.0 °C(Predicted)

Density 

1.177±0.06 g/cm3(Predicted)

storage temp. 

Inert atmosphere,Store in freezer, under -20°C

form 

solid

pka

6.46±0.10(Predicted)

color 

Orange

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

3-OXO-3-(3-PYRIDINYL)PROPANENITRILE Usage And Synthesis

Synthesis

To a stirred solution of methyl nicotinate (XVIII; 8 g; 58 mmol) in toluene (110 mL) at 0 °C was slowly added sodium hydride (2.8 g; 110 mmol). The reaction mixture was kept stirred at 0 °C for 30 min, followed by dropwise addition of acetonitrile (12 g; 91 mmol). The reaction mixture was heated to reflux for 72 hours. After completion of the reaction, the mixture was cooled, concentrated under reduced pressure and diluted with ice-cold water. The pH of the reaction mixture was adjusted to acidic with glacial acetic acid. Subsequently, the aqueous layer was extracted with ethyl acetate (3 x 100 mL). The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give 3-oxo-3-(pyridin-3-yl)propanenitrile (XIX; 6 g, 70% yield) as a yellow solid. Mass spectrometry analysis showed [M-1]? peak at 145.01.

References

[1] Patent: WO2015/97122, 2015, A1. Location in patent: Page/Page column 81; 82
[2] Patent: WO2012/129258, 2012, A1. Location in patent: Page/Page column 150; 151

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