1-Isoquinolinecarbonitrile → isoquinolin-1-ylmethanamine

Participants

Reaction Steps

To a solution of 0.4999 g (3.24 mmol) 1-isoquinolinecarbonitrile (1) (Aldrich) in 15 mL glacial acetic acid was added 0.0564 g Pd (10% on C). After 16 h under H2 at atmospheric pressure, the reaction mixture was filtered over celite. The celite was washed with 75 mL EtOAc, and the filtrate was concentrated in vacuo. To this was added 100 mL n-heptane, and the mixture concentrated in vacuo. The above step was repeated three times to remove acetic acid. Purification by flash chromatography (40×220 mm silica gel, linear gradient 5-10% (10% NH4OH:MeOH):CH2C12) yielded 2. 1H NMR (CDCl3, 400 MHz) δ 8.479 (d, 1H, J=5.76 Hz, ArH); 8.135 (d, 1H, J=8.42 Hz, ArH); 7.848 (d, 1H, J=8.41 Hz, ArH); 7.714-7.673 (m, 1H, ArH); 7.639-7.597 (m, 1H, ArH); 7.563 (d, 1H, J=5.67 Hz, ArH); 4.517 (s, 2H, ArCH2); MS (FAB): m/z 159.08 (M30 H).

Provenance & Evidence