Isoquinoline-8-carbonitrile → Isoquinolin-8-ylmethanamine

Reaction equation

[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[C:11]#[N:12])[CH:4]=[CH:3][N:2]=1>N.[Ni].CCO>[NH2:12][CH2:11][C:9]1[CH:8]=[CH:7][CH:6]=[C:5]2[C:10]=1[CH:1]=[N:2][CH:3]=[CH:4]2

Participants

Procedure

To a solution of 0.1787 g (1.16 mmol) 25 in 10 mL NH3 saturated EtOH was added a 1 mL slurry of Raney nickel (50 wt. % in EtOH). After 22 h under H2 at atmospheric pressure, the reaction mixture was diluted with 25 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 (15×140 mm silica gel, linear gradient 5-8% (10% NH4HO:MeOH):CH2Cl2) afforded 26. 1H NMR (CDCl3, 400 MHz) δ 9.565 (s, 1H, ArH); 8.565 (d, 1H, J=5.66 Hz; ArH); 7.734 (d, 1H, J=8.13 Hz, ArH); 7.679-7.662 (m, 1H, ArH); 7.644 (d, 1H, J=8.14 Hz, ArH); 7.599 (d, 1H, J6.95 Hz, ArH); 4.460 (s, 2H, ArCH2); MS (Electrospray): m/z 159.0 (M+H).