Potassium Nitrate → 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride

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Reaction Steps

A solution of 113(250 mg, 0.63 mmol) in conc. H2SO4 (10 mL) was nitrated with KNO3 (65 mg, 0.65 mmol) in H2SO4 (5 mL) as above, to give 1-(chloromethyl)-5-nitro-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-7-sulfonyl chloride (116) (192 mg, 67%) as a red solid: mp (EtOAc/petroleum ether) 184-189° C.; 1H NMR [(CDCl3)] a 9.34 (s, 1H), 9.28 (d, J=1.8 Hz, 1H), 8.22 (dd, J=9.0, 1.9 Hz, 1H), 8.11 (d, J=9.0 Hz, 1H), 4.77-4.71 (m, 1H), 4.58 (dd, J=11.5, 8.8 Hz, 1H), 4.42-4.33 (m, 1H), 3.95 (dd, J=11.7, 3.5 Hz, 1H 3.73 (dd, J=11.7, 7.7 Hz, 1H); 13C NMR δ 153.4 (q, JC-F 38 Hz), 153.0, 148.2, 147.0, 138.7, 133.2, 129.1, 126.7, 124.5, 122.0, 119.3, 115.9 (q, JC-F 288 Hz), 52.6, 47.3, 41.2. Anal. (C15H9Cl2F3N2O5S) C, H, N, Cl.

Provenance & Evidence