Hydrochloric Acid → HCID 18973026, compound

Participants

Reaction Steps

Pellets of sodium metal (232 mg, 10 mmol) were added to dry ethanol (10 mL) in a dry round-bottomed flask. When dissolution of the sodium was complete, solid 5-chloro-6-azaoxindole (340 mg, 2.0 mmol) was added followed by ethyl 2-thiophenecarboxylate (0.54 mL, 4.0 mmol). The mixture was heated under nitrogen at reflux overnight during which a precipitate formed. The mixture was cooled, poured into ice/water and acidified to pH 4 with 6N HCl solution. The solid product (475 mg) was collected by filtration, washed with water, and dried in the air. This material was recrystallized from methanol to afford the title compound (190 mg, 34%). 1H NMR (DMSO-d6): δ10.62 (br s, 1H), 8.79 (d, J=3.2 Hz, 1H), 7.92 (s, 1H), 7.77 (d, J=5 Hz, 1H), 7.65 (s, 1H), 7.17-7.14 (m, 1H).

Provenance & Evidence