Acetic Acid → HCID 59303232, compound

Participants

Reaction Steps

A solution of 132 (1.54 g, 4.29 mmol) in dioxane (10 mL) was treated with a solution of Cs2CO3 (3.26 g, 10 mmol) in water (3 mL) and MeOH (7 mL) and the mixture was stirred at room temperature for 10 min. The mixture was treated with AcOH (12 mL), then concentrated under reduced pressure to a small volume and partitioned between water and CHCl2. The organic phase was washed with water (×2), dried, and filtered through a column of silica gel. The resulting oil was crystallised from EtOAc/petroleum ether to give 1-(chloromethyl)-9-nitro-1,2-dihydro-3H-benzo[e]indole (136) (1.03 g, 91%) as a red solid: mp 100° C.; 1H NMR [(CD3)2SO] δ 8.07 (dd, J=8.0, 1.1 Hz, 1H), 7.94 (dd, J=7.6, 1.3 Hz, 1H), 7.87 (d, J=8.7H, 1H), 7.21 (t, J=7.8 Hz, 1H), 7.13 (d, J=8.7 Hz, 1H), 6.63 (s, 1H), 3.81-3.71 (m, 1H), 3.71-3.62 (m, 1H), 3.62-3.54 (m, 1H), 3.33-3.25 (m, 2H). Anal. (C13H11ClN2O2) C, H, N.

Provenance & Evidence