Chlorosuccinimide → 3-(3-Methoxy-4-nitrophenyl)-5,6-dihydrobenzo[d]isoxazol-7(4H)-one

Participants

Reaction Conditions

Reaction Steps

To 3-methoxy-4-nitrobenzaldehyde oxime (5.0 g, 25.5 mmol) in DMF (60 ml) at 0° C. was added N-chlorosuccinimide (4.088 g, 30.61 mmol). The reaction mixture was stirred for 15 min at 0° C., and 1.5 hr at ambient temperature. To the reaction flask was added as solids 2-bromocyclohex-2-enone (6.66 g, 38.2 mmol, prepared as in Kowalski, C. J.; Weber, A. E.; Fields, K. W. J. Org. Chem. (1982), 47(26), 5088-93) followed by sodium bicarbonate (4.29 g, 51 mmol), and the mixture was stirred overnight. The reaction mixture was partitioned between water and dichloromethane, the organic phase was washed with water, sat. NaHCO3, and brine. The organic phase was dried over sodium sulfate and concentrated. The residue was chromatographed on silica gel using hexanes/ethyl acetate mixture as eluent to furnish 4.95 g of the title product. 1H NMR (CDCl3) δ: 7.97 (d, J=8.6 Hz, 1H), 7.60 (s, 1H), 7.32 (dd, J=8.4, 1.4 Hz, 1H), 4.05 (s, 3H), 2.99 (t, J=6.1 Hz, 2H), 2.75 (t, J=6.3 Hz, 2H), 2.31 (quin, J=6.3 Hz, 2H).

Provenance & Evidence