Trifluoroacetic acid → 3-(2-Nitrovinyl)-6-ethoxycarbonyl-1H-indole

Participants

Reaction Steps

Combine 1-dimethylamino-2-nitroethylene (1.93 g, 16.58 mmol) and TFA (110.0 ml) and stir until dissolved. Add 6-ethoxycarbonyl-1H-indole (3.14 g, 16.58 mmol) and stir at ambient temperature. After 1 hour, pour the reaction mixture into ice/water, extract with ethyl acetate, then evaporate to residue. Stir the residue in warm ethanol, cool to ambient temperature, then filter and dry to give the title compound as a dark yellow powder: mp 241° C. MS (ACPI): m/e 261.1 (M+1). Analysis for C13H12N2O4: Calcd: C, 60.00; H, 4.65; N, 10.76. found: C, 59.99; H, 4.63; N, 10.59.

Provenance & Evidence