Dimethylformamide → 7-Methoxynaphthalene-1-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-bromo-7-methoxy-naphthalene (3.26 g, 13.8 mmol), Zn(CN)2 (2.26 g, 19.2 mmol), and tetrakis(triphenylphosphine)palladium (1.6 g, 1.4 mmol) in DMF (50 mL) was stirred at 120° C. for 15 hr. The cooled reaction mixture was poured into 200 mL 1 N NH4Cl solution and extracted with ethyl acetate (3×350 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, evaporation of the solvent, and purification on a silica column (10% ethyl acetate—hexanes) yielded 1.28 g (51%) of the title compound as a white solid: mp 62-66° C.; 1H NMR (DMSO-d6): δ 4.00 (3H, s), 7.25 (1H, dd, J=2.48 Hz, J=8.96 Hz), 7.36-7.47 (1H, m), 7.47 (1H, d, J=2.39 Hz), 7.81 (1H, d, J=9.00 Hz), 7.88 (1H, dd, J=0.81 Hz, J=7.23 Hz), 8.00 (1H, d, J=8.21 Hz); MS (EI) m/z 183 (M)+;

Provenance & Evidence