Nitric Acid → 1-(chloromethyl)-3-(trifluoroacetyl)-7-nitro-1,2-dihydro-3H-benzo[e]indole

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Reaction Steps

A stirred solution of 108 (5.24 g, 16.7 mmol) in dry CH2Cl2 (70 mL) was treated dropwise at 10° C. with fuming HNO3 (2.0 mL, 48 mmol) and then warmed to room temperature for 5 min. The mixture was diluted with CH2Cl2 (100 mL) and the resulting solution was washed with water, dried, filtered through a column of silica gel, then concentrated to 25 mL and diluted with EtOAc (25 mL). Following refrigeration the precipitate was collected and washed with EtOAc to give 1-(chloromethyl)-3-(trifluoroacetyl)-7-nitro-1,2-dihydro-3H-benzo[e]indole (131) (2.31 g, 39%) as a pale yellow solid: mp (CH2Cl2/iPr2O) 213-214° C.; 1H NMR [(CD3)2SO] δ 9.06 (s, 1H), 8.48 (d, J=9.0 Hz, 1H), 8.36 (d, J=9.1 Hz, 1H), 8.33-8.25 (m, 2H) 4.67-4.51 (m, 2H), 4.46 (br d, J=10.6 Hz, 1H), 4.17 (dd, J=11.3, 3.0 Hz, 1H), 4.07 (dd, J=11.3, 5.5 Hz, 1H). Anal. (C15H10ClF3N2O3) C, H, N.

Provenance & Evidence