Ammonia → methyl 1-(chloromethyl)-9-nitro-1,2-dihydro-3H-benzo[e]indole-7-carboxylate

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Reaction Conditions

Reaction Steps

Powdered 150 (900 mg, 2.39 mmol) was added to stirred conc. H2SO4 (6 mL) at 0° C. and the mixture was warned to room temperature for 15 nm. The resulting solution was cooled to −5° C. and treated dropwise with a solution of KNO3 (266 mg, 2.63 mmol) in conc. H2SO4 (1.5 mL). The mixture was stirred at −5° C. for a further 5 min, then poured into ice/water and neutralized with dilute aqueous NH3. The resulting solid was chromatographed on silica gel, eluting with CH2Cl2 to give crude methyl 1-(chloromethyl)-9-nitro-1,2-dihydro-3H-benzo[e]indole-7-carboxylate (151) (102 mg, 13%) as an orange-brown solid; 1H NMR [(CD3)2SO] δ 8.66 (d, J=1.7 Hz, 1H), 8.30 (d, J=1.7 Hz, 1H), 8.08 (d, J=8.8 Hz, 1H), 7.25 (s, 1H), 7.18 (d, J=8.8 Hz, 1H), δ 3.92-3.83 (m, 4H), 3.74-3.67 (m, 1H), 3.63 (dd, J=10.6, 2.3 Hz, 1H), 3.39-3.28 (m, 2 H).

Provenance & Evidence