Hydrochloric Acid → 4-(5-nitro-1H-indol-3-yl)cyclohex-3-en-1-one

Participants

Reaction Steps

A solution of compound 78 (0.1 g, 0.332 mmol) in acetone (5 mL) was treated with 10% aq. HCl (5 mL) at room temperature and stirred for 6 h. Acetone was evaporated and crude was basified using NH4OH solution (20 mL). The product was extracted into CH2Cl2 (2×20 mL), washed with brine (10 mL) and dried (Na2SO4). The CH2Cl2 layer was evaporated to obtain compound 79 (0.075 g, 88%) as a solid. mp 210-212° C.; 1H NMR (DMSO-d6) δ 2.59 (t, 2H, J=6.9 Hz), 2.90 (t, 2H, J=6.6 Hz), 3.11-3.12 (m, 2H), 6.24 (t, 1H, J=3.6 Hz), 7.57 (d, 1H, J=9.0 Hz), 7.76 (d, 1H, J=2.1 Hz), 8.03 (dd, 1H, J=2.1, 9.0 Hz), 8.71 (d, 1H, J=2.1 Hz), 11.95 (s, 1H); ESI-MS m/z (%): 257 (M+, 100).

Provenance & Evidence