2-Naphthonitrile

2-Naphthonitrile is prepared as follows:

In a glove box filled with N2, NiCl2·6H2O (5.9 mg, 0.025 mmol), dppf (16.6 mg, 0.03 mmol), Zn (6.5 mg, 0.1 mmol), Zn(CN)2 (47.0 mg, 0.4 mmol), DMAP (91.6 mg, 0.75 mmol), 2-naphthylmethylsulfonate (0.5 mmol), and CH3CN (5 mL) were added sequentially to a sealed vial. After sealing, the vial was removed from the glove box and placed directly in a 50°C oil bath for heating. After 8 hours, the reaction was cooled to room temperature, analyzed by TLC, filtered through silica gel, washed with ethyl acetate, concentrated, and then subjected to column chromatography. Silica gel plate chromatography, eluent: petroleum ether/ethyl acetate = 35:1, yielded 71.6 mg of a white solid 2-naphthoonitrile, with a yield of 93%. ¹H NMR purity was greater than 98%.

off-white to beige crystalline powder

2-Cyanonaphthalene [613-46-7], bnaphthonitrile, 2-naphthoic acid nitrile, Mr 153.17, mp 66℃, bp 303℃, forms colorless crystals that are readily soluble in ethanol. It is used in organic synthesis and suitable as a reaction medium for obtaining propylene from ethylene and 2-butene by olefin metathesis.

Journal of the American Chemical Society, 112, p. 6729, 1990 DOI: 10.1021/ja00174a053
Synthesis, p. 223, 1989 DOI: 10.1055/s-1989-27210