After stirring for 3 d at 100 ◦C the solvent was evaporated.
The crude hydrazone was dissolved in 12 g, 4 wt% H2SO4 in
anhydrous THF. After stirring for 3 h at reflux temperature the
reaction mixture was washed with aqueous ammonia and dried
over MgSO4. The solvent was evaporated and the residue was
purified by flash chromatography on silica to yield 0.64 g (98%) 2-
(toluene-4-sulfonyl)-2,3,4,9-tetrahydro-1H-b-carboline (30d): 1H-
NMR (500 MHz, DMSO): d [ppm] = 2.34 (s, 3 H, CH3), 2.65–2.73
(2 H, CH2), 3.28–3.47 (2 H, CH2), 4.25 (s, 2 H, CH2), 6.93 (dd,
3J = 7.3; 8.0 Hz, 1 H, CH), 7.02 (dd, 3J = 7.3; 7.7 Hz, 1 H, CH),
7.27 (d, 3J = 8.0 Hz, 1 H, CH), 7.31 (d, 3J = 7.7 Hz, 1 H, CH),
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3
3
7.40 (d, J = 8.0 Hz, 2 H, 2 × CH), 7.69 (d, J = 8.0 Hz, 2 H,
2 × CH), 10.78 (bs, 1 H, NH). 13C-NMR (125 MHz, DMSO): d
[ppm] = 20.9 (CH2), 21.0 (CH3), 43.4 (CH2), 44.1 (CH2), 106.3
(Cq), 111.2 (CH), 117.7 (CH), 118.7 (CH), 121.1 (CH), 126.3 (Cq),
127.3 (2 × CH), 129.3 (Cq), 130.0 (2 × CH), 133.7 (Cq), 136.0 (Cq),
143.7 (Cq). MS (FAB): m/z (%) = 327 (M + H+, 25), 326 (M+,
21), 155 (100). IR: m˜ [cm−1] = 3390 (m), 3047 (w), 2909 (w), 1596
(m), 1451 (m), 1345 (s), 1165 (vs), 1092 (m), 746 (s). HR-MS (EI):
calculated for C18H19NO2S 327.1167 g mol−1; found: 327.1172 g
mol−1. Structure was clarified by 1D-NOESY experiments.
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