3-(2-PYRIDYL)-3-OXOPROPANENITRILE Chemical Properties

Melting point:

97-99°C

Boiling point:

312.7±22.0 °C(Predicted)

Density 

1.177±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2-8°C

pka

6.05±0.10(Predicted)

Appearance

Brown to black Solid

Safety Information

Hazard Codes 

Xi

HazardClass 

IRRITANT

HS Code 

2933399990

3-(2-PYRIDYL)-3-OXOPROPANENITRILE Usage And Synthesis

Application

3-(2-PYRIDYL)-3-OXOPROPANENITRILE can be used as an organic synthesis intermediate and a pharmaceutical intermediate in laboratory research and development processes and in the synthesis of pharmaceutical chemicals.

Synthesis

Preparation of Intermediate 35 [General Procedure 14]: Intermediate 34 (3 g, 19.6 mmol) and acetonitrile (0.8 mL, 19.6 mmol, 1 equiv) were dissolved in toluene (10 mL) under dry conditions. This solution was slowly added to a mixture of sodium hydride (784 mg, 19.6 mmol, 1 equiv, 60% mineral oil dispersion) pre-suspended in toluene (50 mL) and the reaction temperature was maintained at 65 °C. The reaction mixture was stirred continuously at 65°C for 16 hours. Upon completion of the reaction, the mixture was cooled to room temperature and the reaction was quenched with ice-cold water (20 mL). The resulting solid was collected by filtration to afford Intermediate 35 (1.5 g, 53% yield) as a brown solid. The product was characterized by 1H NMR (CDCl3): δ 8.70 (d, J = 4.8Hz, 1H), 8.12 (d, J = 7.5Hz, 1H), 7.90-7.94 (m, 1H), 7.56-7.60 (m, 1H), 4.41 (s, 2H). Mass spectrometry analysis showed a molecular ion peak [M + H]+ of 147. Thin layer chromatography (TLC) analysis was performed with ethyl acetate as the unfolding agent and an Rf value of 0.40.

References

[1] Tetrahedron Letters, 2006, vol. 47, # 15, p. 2531 - 2534
[2] Patent: WO2011/126903, 2011, A2. Location in patent: Page/Page column 100
[3] Patent: WO2014/145986, 2014, A1. Location in patent: Paragraph 0267; 0268
[4] Patent: US2017/326125, 2017, A1. Location in patent: Paragraph 0406-0408
[5] Patent: US2014/179676, 2014, A1. Location in patent: Paragraph 0898; 0908

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