Hydrochloric Acid → HCID 178513238, compound

Participants

Reaction Conditions

Reaction Steps

5-Cyanoindole (1.00 g), hydroxylamine.HCl (978 mg) and NaHCO3 (2.95 g) were dissolved/suspended in MeOH (14 ml), heated to 50° C. and stirred overnight. LCMS analysis showed the reaction was incomplete after this time so a further portion of hydroxylamine.HCl (978 mg) was added and the reaction temperature raised to 80° C. The reaction was complete after 4 hours. The reaction mixture was cooled to RT and evaporated to dryness under reduced pressure. The residue was treated with 1M aqueous HCl (50 ml) and extracted with EtOAc (2×50 ml). This failed to extract the product from the aqueous solution so it was treated with 2M aqueous NaOH to adjust the pH to approximately 7 then re-extracted with EtOAc (3×50 ml). The combined organics were washed with brine (30 ml), dried over MgSO4, filtered and evaporated to dryness to give the title compound (1.36 g) as a brown oil. δH (MeOD, 400 MHz) 6.50 (1H, s), 7.27 (1H, s), 7.36-7.45 (2H, m), 7.88 (1H, s). MS (ES): C9H8N3O requires 175; found 176 (MH+).

Provenance & Evidence