Hydrochloric Acid → HCID 10750709, compound

Participants

Reaction Steps

Tin powder (2.65 g, 22.3 mmol) was added to a suspension of nitroindole 44 (600 mg, 2.56 mmol) in EtOH (90 mL). Hydrochloric acid (3 M, 36 mL) was added and the mixture was stirred at room temperature for 2 h. The reaction mixture was decanted from the excess tin and added in portions to saturated sodium bicarbonate (200 mL). The mixture was extracted with EtOAc (4×) and the combined extracts were washed with sodium bicarbonate (1 M, 3×) and saturated NaCl (2×), dried (MgSO4), filtered and evaporated. Compound 45 was isolated as a dark yellow oil (513 mg, 98%) and used in the following reaction without further purification; Rf=0.67 (EtOAc); 1H NMR (CDCl3): δ 9.61 (s, 1H), 7.55 (s, 1H), 6.94 (d, 1H, J=8.6 Hz), 6.53 (d, 1H, J=8.6 Hz), 5.79 (bs, 2H), 3.88 (s, 3H), 3.76 (s, 3H).

Provenance & Evidence