Potassium Nitrate → HCID 44549394, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of 102 (500 mg, 1.90 mmol) in conc. H2SO4 (5 mL) was cooled to −5° C. and treated with powdered KNO3 (288 mg, 2.85 mmol). The mixture was stirred at 0° C. for a further 15, in, then poured into ice-water and the solid was collected and dissolved in CH2Cl2. The solution was filtered through a column of silica gel and the product was recrystallised from EtOAc/iPr2O to give 1-(chloromethyl)-5,6-dinitro-1,2-dihydro-3H-benzo[e]indole (103) (446 mg, 76%) as a red solid: mp 206-207° C.; 1H NMR [(CD3)2SO] δ 8.23 (dd, J=8.7, 1.0 Hz, 1H), 8.00 (dd, J=7.7, 0.9 Hz, 1H), 7.76 (s, 1H), 7.67 (dd, J=8.4, 7.6 Hz, 1H), 6.72 (s, 1H), 4.32-4.22 (m, 1H), 3.94-3.83 (m, 2H), 3.83-3.75 (m, 2). Anal. (C13H10ClN3O4) C, H, N.

Provenance & Evidence