Potassium Carbonate → 4-(4-Methoxy-benzylamino)-nicotinonitrile

Participants

Reaction Steps

A solution of 4-chloronicotinonitrile (1.00 g, 7.22 mmol), 4-methoxybenzylamine (1.03 ml, 7.94 mmol) and potassium carbonate (1.20 g, 8.66 mmol) in propan-2-ol (20 mL) was heated under reflux for 18 hours. The solvent was concentrated in vacuo and the residue partitioned between EtOAc (150 mL) and water (50 mL). The organic phase was dried (Na2SO4), filtered and evaporated to give a brown oil. The oil was pre-adsorbed onto H-MN and purified by flash column chromatography (Si-PPC, cyclohexane:EtOAc, gradient 80:20 to 0:100) to provide the title compound as a white solid (1.61 g, 93%). 1H NMR (CDCl3, 300 MHz) 8.46 (d, J=0.7 Hz, 1H), 8.30 (dd, J=6.1 Hz, 0.7 Hz, 1H), 7.24 (dd, J=8.6 Hz, 2.1 Hz, 2H), 6.92 (dd, J=8.6 Hz, 2.1 Hz, 2H), 6.55 (d, J=6.1 Hz, 1H), 5.35 (br t, 1H), 4.40 (d, J=5.6 Hz, 2H), 3.82 (s, 3H).

Provenance & Evidence