Ammonia → 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide

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Reaction Steps

Conc. aqueous NH3 (0.5 mL, 7.3 mmol) was added to a solution of 116 (299 mg, 0.65 mmol) in THF (10 mL) at 0° C., and the ice bath was removed. The mixture was stirred for 7 min and then Cs2CO3 (0.55 g, 1.7 mmol) and MeOH (4 mL) were added. After stirring for a further 15 min the mixture was diluted with brine and extracted with CH2Cl2 (×3). The combined extracts were dried and evaporated to give 1-(chloromethyl)-5-nitro-1,2-dihydro-3H-benzo[e]indole-7-sulfonamide (117) (214 mg, 96%) as an orange solid. A sample was triturated with EtOAc: mp 183-187° C. (dec.); 1H NMR [(CD3)2SO] δ 8.59 (d, J=1.7 Hz, 1H), 8.03 (d, J=8.9 Hz, 1H), 7.85 (dd, J=8.9, 1.7 Hz, 1H), 7.75 (s, 1H), 7.42 (s, 2H), 6.68 (s, 1H), 4.28-4.21 (m, 1H), 3.95-3.85 (m; 2H), 3.81 (dd, J=11.2, 8.3 Hz, 1H), 3.73 (dd, J=10.4, 3.0 Hz, 1H). Anal. (C13H12ClN3O4S) C, H, N.

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