Nitric Acid → 3-(4-Nitrophenyl)pyridine

Participants

Reaction Steps

To a solution of H2SO4 (6 mL) cooled in an ice bath to 0° C. was added 3-phenylpyridine (1.0 g, 6.4 mmol). The orange-red solution was vigorously stirred while HNO3 (1 mL) was slowly added dropwise to give a cloudy light yellow solution. After stirring at room temperature for 20 min the solution was carefully poured into a beaker filled with ice (200 g). The solution was neutralized with 20% NaOH to give a cloudy white suspension which was extracted with EtOAc (3×150 mL). The organic layers were combined, washed with brine (2×50 mL), dried (NaSO4) and concentrated in vacuo to give the desired product (1.2 g, 99%) as a light yellow solid. Data for 3-(4-nitrophenyl)pyridine: Rf =0.47 (silica gel, methanol/CHCl3, 5/95); 1H NMR (400 MHz, acetone-d6) 8.99 (s, 1 H), 8.67 (s, 1 H), 8.37 (d, J=7.0, 2 H), 8.18 (m, 1 H), 8.02 (d, J=7.0, 2 H), 7.53 (m, 1 H).

Provenance & Evidence