Sulfuric Acid → HCID 44549271, compound

Participants

Reaction Conditions

Reaction Steps

Solid 126 (500 mg, 1.48 mmol), was added to 90% H2SO4 (5 μL) and heated to 70° C. for 1 h. After cooling to room temperature, the mixture was poured into ice-water and extracted with EtOAc (3×50 mL). The extracts were dried and concentrated under reduced pressure. Chromatography of the residue on silica gel (EtOAc/petroleum ether, from 1:1 to 1:0) gave 1-(chloromethyl)-3-(trifluoroacetyl)-1,2-dihydro-3H-benzo[e]indole-6-carboxamide (128) (410 mg, 78%) as a white solid: mp (EtOAc/petroleum ether) 190-193° C.; 1H NMR (CDCl3) δ 8.54-8.45 (m, 2H), 7.89 (d, J=5.8 Hz, 1H), 7.69 (dd, J=7.1, 1.1 Hz, 1H), 7.59 (dd, J=8.4, 7.1 Hz, 1H), 5.91 (br, 2H), 4.69-4.61 (m, 1H), 4.48-4.40 (m, 1H), 4.25-4.17 (m, 1H), 3.97-3.89 (m, 1H), 3.58-3.50 (m, 1H; 13C NMR δ 170.7, 153.8 (q, JC-F 38.0 Hz), 140.5, 134.6, 129.7, 128.6, 126.5, 125.6, 125.4, 124.8, 118.4, 115.4 (q, JC-F 288 Hz), 53.4, 45.4, 43.0. Anal. (C16H12ClF3N2O2) C, H, N, Cl.

Provenance & Evidence