Nitrogen → HCID 13802441, compound

Participants

Reaction Steps

A mixture of 1-chloro-2-methoxy-4-nitrobenzene (2.71 g, 14.47 mmol) and 2,5-dihydro-1H-pyrrole (2.0 g, 28.9 mmol) was stirred at 100° C. under a stream of N2 for 10 h. The reaction was cooled to RT to give a brown solid which was dissolved in CH2Cl2 (200 mL), washed with 100 mL of 1 N NaOH solution and brine, dried over MgSO4, and concentrated. The resulting brown oil was purified by flash chromatography (silica gel, Hexanes:EtOAc, 100:0 to 80:20) to afford the title compound (2.67 g, 84% yield) as a orange solid: 1H NMR (500 MHz, CDCl3) δ 7.84 (dd, J=8.80, 2.50 Hz, 1H), 7.65 (d, J=2.50 Hz, 1H), 6.39 (d, J=8.80 Hz, 1H), 5.89 (s, 2H), 4.46 (s, 4H), 3.83 (s, 3H). HPLC retention time: 3.315 min; LCMS (ES): m/z 221 [M+H]+.

Provenance & Evidence