6-phenylpyridine-2-carbonitrile synthesis
- Product Name:6-phenylpyridine-2-carbonitrile
- CAS Number:39065-47-9
- Molecular formula:C12H8N2
- Molecular Weight:180.21
Yield:39065-47-9 86%
Reaction Conditions:
with potassium carbonate;tetrakis(triphenylphosphine) palladium(0) in ethanol;water;toluene; for 16 h;Heating / reflux;
Steps:
66 Reference Example 66
Reference Example 66 6-Phenyl-2-pyridinecarbonitrile 6-Chloro-2-pyridinecarbonitrile (0.80 g, 5.7 mmol) and phenylboric acid (1.05 g, 8.6 mmol) were dissolved in toluene (60 ml)-ethanol (15 ml), and potassium carbonate (2.00 g, 14.4 mmol) and water (15 ml) were added thereto.. The mixture was deairated under reduced pressure for 10 minutes. tetrakis(triphenylphosphine)palladium (0) (0.33 g, 0.29 mmol) was added to the reaction mixture under argon atmosphere, and the mixture was refluxed for 16 hrs.. The reaction mixture was combined with ethyl acetate and water.. The organic layer was washed with saturated brine and dried over anhydrous magnesium sulfate.. The solvent was evaporated, and the residue was subjected to a silica gel column chromatography.. The fractions eluted with hexane-ethyl acetate (4:1, v/v) were collected, concentrated and recrystallized from hexane-ethyl acetate to give the titled compound (0.90 g, 86 %). mp. 65.2-66.1 °C1H-NMR (CDCl3) δ: 7.48-7.51 (3H, m), 7.62 (1H, dd, J = 1.1, 7.3 Hz), 7.85-7.93 (2H, m), 8.01-8.04 (2H, m) IR(KBr): 3067, 2235, 1581, 1556, 1448, 817, 762 cm-1.
References:
EP1424336,2004,A1 Location in patent:Page 149
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