Dimethylformamide → 5-Cyanoquinoline

Participants

Reaction Steps

To a solution of 0.1810 g (0.870 mmol) 10 in 5 mL DMF was added 0.0630 g (0.54 mmol) zinc cyanide and 0.0640 g (0.055 mmol) tetrakis(triphenylphosphine)palladium(0). After 66 h under argon at 80° C., the reaction mixture was cooled to room temperature, diluted with 40 mL toluene and washed with 10 mL 2N NH4H. The aqueous layer was extracted with 10 mL toluene. The combined organic layers were washed with 10 mL brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (25×130 mm silica gel, linear gradient 2-3% (10% NH4OH:MeOH):CH2Cl2) afforded 11. 1NMR (CDCl3, 400 MHz) 69.065 (dd, 1H, J=1.65, 4.21 Hz, ArH); 8.567 (d, 1H, J=8.50 Hz, ArH); 8.377 (d, 1H, J=8.50 Hz, ArH); 8.005 (dd, 1H, J=1.09, 7.22 Hz, ArH); 7.796 (dd, 1H, J=7.22, 8.59 Hz, ArH); 7.636 (dd, 1H, J=4.21, 8.51 Hz, ArH); MS (Electrospray): m/z 155.0 (M+H).

Provenance & Evidence