Pyridine-2-carbonitrile → HCID 178420129, compound

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Reaction Steps

A 250 ml reaction flask is dried under vacuum and baked by fire and then cooled by nitrogen gas flow. 50 ml of anhydrous ether is added into the flask and (trimethylsilyl)diazomethane (6 ml, 12.0 mmol) is also added. At −78° C., n-butyl lithium agent (6 ml, 14.4 mmol) is added. After reacting for 0.5 hrs, 2-cyanopyridine (1.04 g, 10.0 mmol) is added. The reaction is then carried out for 12 hrs. After the reaction is finished, ether extraction is carried out and the organic layer is collected and then concentrated to obtained white solids. The white solids are placed in a 50 ml reaction flask, potassium fluoride (0.58 g, 10.0 mmol) is added, 10 ml of ethanol is added, and a few drops of hydrochloride are added. Hot reflux is carried out for 2 hrs. After the reaction is finished, the reaction solution is neutralized by saturated sodium bicarbonate solution. Ether extraction is carried out and the organic layer is collected and then concentrated to obtain white solids. After purified by silicone chromatographic column, the product pytz is obtained. The yield is about 60%. 1H NMR (500 MHz, CDCl3): δ 8.70 (s, 1 H), 8.36 (s, 1 H), 7.99 (s, 1 H), 7.82 (t, 1 H, J=8.0 Hz), 7.32-7.29 (m, 1 H). HRMS (EI) m/z:calculated value C7H6N4 146.0592; experimental value 146.0593.

Provenance & Evidence