| Identification | Back Directory | [Name]
3-OXO-3-PYRIDIN-4-YL-PROPIONITRILE | [CAS]
23821-37-6 | [Synonyms]
4-(2-Cyanoacetyl)pyridine
b-oxo-4-Pyridinepropanenitrile
4-Pyridinepropanenitrile, β-oxo-
3-Oxo-3-(4-pyridyl)propanenitrile
Beta-oxo-4-pyridinepropanenitrile
3-OXO-3-PYRIDIN-4-YLPROPANENITRILE
3-OXO-3-PYRIDIN-4-YL-PROPIONITRILE
3-OXO-4-PYRIDIN-3-YL-PROPIONITRILE
3-Oxo-3-(4-pyridinyl)propanenitrile
3-oxo-3-(yridine-4-yl)propanenitrile
4-Pyridinepropanenitrile, .beta.-oxo-
3-Oxo-3-(pyridin-4-yl)propionitrile, 4-(Cyanoacetyl)pyridine | [Molecular Formula]
C8H6N2O | [MDL Number]
MFCD06656807 | [MOL File]
23821-37-6.mol | [Molecular Weight]
146.15 |
| Chemical Properties | Back Directory | [Boiling point ]
335.3±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]
6.29±0.10(Predicted) | [Appearance]
Light yellow to orange Solid |
| Hazard Information | Back Directory | [Synthesis]
3-Oxo-3-(4-pyridyl)propionitrile was synthesized from methyl isonicotinate and acetonitrile according to the improved scheme of route A1. The procedure was as follows: 3 g (22 mmol) of methyl isonicotinate was dissolved in 30 mL of anhydrous toluene under nitrogen protection, and 1.75 g (44 mmol) of 50-60% NaH (dispersed in mineral oil) was slowly added. Subsequently, 5.39 mL (103 mmol) of dry acetonitrile was added slowly and dropwise at 90 °C. The reaction mixture was heated and refluxed for 18 hours, during which the product precipitated as sodium salt. After completion of the reaction, it was cooled to room temperature and the solid product was collected by filtration. The solid was dissolved in water, the pH was adjusted to 5-6 with 6N HCl solution and the product was extracted with dichloromethane (DCM). The aqueous phase was again pH adjusted to 4-5 and a secondary extraction with DCM was performed to recover more product. The organic phases were combined, dried over anhydrous sodium sulfate and concentrated to give the crude product in 58% yield. The crude product can be used directly in the subsequent reaction. | [References]
[1] Patent: WO2008/87529, 2008, A1. Location in patent: Page/Page column 113
[2] Patent: WO2007/98826, 2007, A2. Location in patent: Page/Page column 47-48
[3] Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 24, p. 6890 - 6892
[4] Patent: WO2006/84015, 2006, A2. Location in patent: Page/Page column 86-87
[5] Patent: WO2010/9290, 2010, A1. Location in patent: Page/Page column 143-144 |
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