5-Cyanoquinoline → 1-(Quinolin-5-yl)methanamine

Participants

Reaction Steps

To a solution of 0.1173 g (0.76 mmol) 11 in 10 mL NH3 saturated EtOH was added a 1 mL slurry of Raney nickel (50wt. % in EtOH). After 19 h under H2 at atmospheric pressure, the reaction mixture was diluted with 20 mL EtOH and filtered over celite. The celite was washed with 200 mL EtOH, and the filtrate was concentrated in vacuo. Purification by flash chromatography (20×120 mm silica gel, linear gradient 5-7% (10% NH4OH:MeOH):CH2C2) provided 12. 1H NMR (CDCl3, 400 MHz) δ 8.937 (dd, 1H, J=1.56, 4.12 Hz, ArH); 8.475 (d, 1H, J=8.14 Hz, ArH); 8.033 (d, 1H, J=8.50 Hz, ArH); 7.681 (t, 1H, J=7.78 Hz, ArH); 7.546 (d, 1H, J=7.04 Hz, ArH); 7.450 (dd, 1H, J=4.16, 8.55 Hz, ArH); 4.347 (s, 2H, ArCH2); MS (Electrospray): m/z 159.0 (M+H).

Provenance & Evidence