Reaction Steps
A suspension of quindoline (1 g, 4.6 mmol) from Example 2 and butyl iodide (3 ml, 26.4 mmol) was heated in a bomb at 140° C. for 16 hours and then cooled. The solid was filtered, washed thoroughly with ether, washed with 10% EtOH in ethyl ether and then dried to afford 5-butylquindolinium hydroiodide, 1.82 g (100%) as a brown solid. Recrystallization from water gave bright yellow crystals of 5-butylquindolinium hydroiodide, mp 252-253° C.; 1H NMR (DMSO-d6) δ 12.96 (s, 1H, NH), 9.34 (s, 1H, H11), 8.77 (d, J=9.2, 1H, H4), 8.61 (d, J=8.4, 1H, H6), 8.54 (d, J=8.4, 1H, H1), 8.19 (t, J=8.4, 1H, H3), 7.96 (t, J=8.4, J=7.2, 2H, H2 and H8), 7.88 (d, J=8.4, 1H, H9), 7.58 (t, J=7.2, 1H, H7), 5.51 (t, J=7.2, 2H, N--CH2), 2.09 (m, 2H), 1.69 (m, 2H), 1.00 (t, J=7.2, 3H, CH3); 13C NMR (DMSO-d6) δ 145.78, 137.07, 134.64, 133.93, 133.52, 132.71, 130.07, 127.11, 126.40, 125.38, 125.29, 121.88, 117.55, 113.47,112.89, 51.29, 30.11, 19.22, 13.83; MS (EI, m/z) 275 (M+)
