Water → 5-Cyanoquinoline

Participants

Reaction Steps

A mixture of 5-iodoquinoline (0.56 g; 2.2 mmol) and CuCN (0.51 g; 5.7 mmol) in anhydrous DMF (3 ml) was refluxed for 40 min under N2. After cooling to room temperature, the mixture was diluted to 20 ml with EtOAc and NaCN (0.75 g; 15.3 mmol) was added followed by H2O (10 ml). The resulting mixture was vigorously stirred for 10 min and organic phase was separated, washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness to give the title compound (0.33 g; 97%) as colourless solid. 1H-NMR (CDCl3) 7.59-7.63 (m, 1H); 7.78 (m, 1H); 7.98 (dd, 1H, J=3, 6 Hz); 8.36 (d, 1H, J=9 Hz); 8.54 (m, 1H): 9.05 (dd, 1H, J=3, 6 Hz).

Provenance & Evidence