Hydrochloric Acid → 4-(6-Bromo-3,4-dihydroquinolin-1(2H)-yl)cyclohexanone

Participants

Reaction Steps

A solution of compound 4 (0.21 g, 0.596 mmol) in acetone (5 mL) was treated with 10% HCl solution (5 mL) and the resulting mixture was stirred for overnight (16 h). Acetone was evaporated, the crude was basified with 2 N NaOH solution and the product was extracted into CH2Cl2 (2×15 mL). The combined CH2Cl2 layer was washed with brine (10 mL) and dried (Na2SO4). The solvent was evaporated to obtain compound 5 (0.18 g, 98%) as a syrup. 1H NMR (CDCl3) δ 7.16 (dd, 1H, J=2.4, 4.3 Hz), 7.08 (s, 1H), 6.60 (d, 1H, J=9.0 Hz), 4.11-4.01 (m, 1H), 3.17 (t, 2H, J=5.7 Hz), 2.71 (t, 2H, J=6.3 Hz), 2.52-2.48 (m, 4H), 2.14-1.85 (m, 6H); ESI-MS (m/z, %): 308, 310 (MH+, 100).

Provenance & Evidence