Methanol → 2-Methoxy-6-nitrobenzonitrile

Participants

Reaction Steps

A solution of sodium methoxide, obtained by adding sodium (1.68 g, 73.1 mmol) to anhydrous MeOH (73 mL), was added to 2,6-dinitrobenzonitrile (13.20 g, 68.4 mmol) in dry MeOH (284 mL) under nitrogen at room temperature over 10 min. The reaction was refluxed for 1 hour, and then MeOH was removed under vacuum. Dichloromethane (400 mL) was added, and the insoluble solids were filtered out. The organic layer was washed with brine (100 mL), dried with MgSO4, and removed under vacuum to give 11.45 g (94%) of 2-methoxy-6-nitrobenzonitrile, which was used without further purification. 1H-NMR (400 MHz, DMSO-d6) δ 7.87-7.94 (m, 2H), 7.68-7.75 (m, 1H), 4.01 (s, 3H).

Provenance & Evidence