Potassium Nitrate → HCID 44549537, compound

Participants

Reaction Conditions

Reaction Steps

A stirred solution of amine 136 (900 mg, 3.43 mmol) in conc. H2SO4 (9 mL) was cooled to −5° C. and treated with powdered KNO3 (520 mg, 5.14 mmol). The mixture was stirred at 0° C. for a further 15 min, then poured into ice-water and the solid was collected Chromatography on silica gel, eluting with petroleum ether/EtOAc (3:1), followed by two recrystallizations from CH2Cl2/iPr2O gave 1-(chloromethyl)-5,9-dinitro-1,2-dihydro-3H-benzo[e]indole (137) (394 mg, 37%) as a red solid: mp 130-131° C.; 1H [(CD3)2SO] δ 8.21 (dd, J=8.6, 1.1 Hz, 1H), 8.10 (dd, J=7.6, 1.1 Hz, 1 H), 7.75 (s, 1H), 7.44 (dd, J=−8.6, 7.6 Hz, 1H), 7.02 (s, 1H), 3.89-3.81 (m, 1H), 3.72-3.62 (m, 2H), 3.41-3.35 (m, 2H). Anal. (C13H10ClN3O4) C, H, N, Cl.

Provenance & Evidence