Hydroxyamine hydrochloride → Ethyl 4-cyano-5-methyl-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

Ethyl 4-formyl-5-methyl-1H-pyrrole-2-carboxylate (Intermediate 15, 0.2 g, 1.1 mmol) and hydroxylamine hydrochloride (0.08 g, 1.1 mmol) were dissolved in EtOH (10 ml) and refluxed for 1.5 hours. The mixture was concentrated under vacuum to give yellow solid, which was dissolved in DMF (5 ml) before addition of SOCl2 (0.35 ml) at 0° C. The solvent was removed under vacuum after the completion of the reaction and the residue was partitioned between water and EtOAc. The layers were separated and the aqueous layer was extracted with EtOAc twice. The combined organic extracts were dried over MgSO4 and concentrated to give brown solid (0.16 g, crude).

Provenance & Evidence