Acetic Acid → tert-butyl 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-carbamate

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Reaction Steps

A suspension of 221(218 mg, 0.46 mmol) in dioxane (5 mL) was treated at room temperature with a solution of Cs2CO3 (0.33 g, 1.0 mmol) in water (1 mL) and MeOH (9 mL). The mixture was stirred at room temperature for 5 min and then treated with AcOH (0.15 mL) and diluted with water. The precipitate was collected and crystallised from CH2Cl2/hexane to give tert-butyl 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-carbamate (222) (164 mg, 94%) as a red solid: mp 162-163° C. (dec.); 1H NMR [(CD3)2SO] δ 9.57 (s, 1H), 8.46 (d, J=1.7 Hz, 1H), 7.81 (d, J=9.1 Hz, 1H), 7.65-7.57 (m, 2H), 6.09 (d, J=2.1 Hz, 1H), 4.19-4.10 (m, 1H), 3.88 (dd, J=10.9, 3.7 Hz, 1H), 3.81-3.63 (m, 3H), 1.50 (s, 9H). Anal. (C18H20ClN3O4) C, H, N.

Provenance & Evidence