8-(Azidomethyl)quinoline → (Quinolin-8-yl)methanamine

Participants

Reaction Steps

To a solution of 0.8432 g (4.58 mmol) 21 in 20 mL EtOAc was added 0.0880 g Pd (10% on C). After 19 h under H2 at atmospheric pressure, the reaction mixture was diluted with 25 mL EtOAc and filtered over celite. The celite was washed with 150 mL EtOAc, and the combined organics were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (40×140 mm silica gel, linear gradient 5-15% (10% NH4OH:MeOH):CH2Cl2) gave 22. 1H NMR (CDCl3, 400 MHz) δ 8.936 (dd, 1H, J=1.78, 4.16 Hz, ArH); 8.165 (dd, 1H, J=1.69, 8.28 Hz, ArH); 7.730 (dd, 1H, J=1.10, 8.14 Hz, ArH); 7.652 (dd, 1H, J=0.64, 7.03 Hz, ArH); 7.497 (t, 1H, J=7.59 Hz, ArH); 7.421 (dd, 1H, J=4.22, 8.23 Hz, ArH); 4.433 (s, 2H, ArCH2); MS (FAB): m/z 159.09 (M+H).

Provenance & Evidence