Hydrochloric Acid → Ethyl 1H-pyrrolo(2,3-b)pyridine-2-carboxylate

Participants

Reaction Steps

To a stirred solution of (RS) ethyl (2-hydroxy-1-tert-butoxycarbonyl-7-azaindoline-2-carboxylate) (0.6 g, 1.9 mmol) in ethanol (20 mL) was added dropwise concentrated hydrochloric acid (0.6 mL). The mixture was heated under reflux for 2 h, cooled to room temperature and partitioned between ether (30 mL) and aqueous sodium hydrogen carbonate solution (30 mL). The organic layer was washed (water, brine), dried (sodium sulfate) and concentrated in vacuo to give ethyl 7-azaindole-2-carboxylate as a white solid (0.26 g, 70%). mp 153–6° C. Found: C, 62.84; H, 5.34; N, 14.50%. C10H10N2O2 requires: C, 63.15; H, 5.30; N, 14.72%.

Provenance & Evidence