Hydroxylamine → HCID 3013464, compound

Participants

Reaction Steps

To a stirred solution of ethyl 9H-β-carboline-3-carboxylate (370 mg, 1.54 mmol) in DMF (5 mL) under a nitrogen atmosphere was added NaH (61.6 mg, 60% in mineral oil, 1.54 mmol) portionwise, followed by 2,4-difluorobenzyl bromide (198 μL, 1.54 mmol). Stirring was continued for 48 hours at ambient temperature, water (100 mL) was then added to the mixture. The precipitate was filtered, washed with water and dried to give a solid that was dissolved in methanol (35 mL). To the resulting solution, H2NOH (30 mL, 50 wt. % solution in H2O, 0.45 mol) was added. The suspension was stirred for 4 days at ambient temperature. The mixture was then filtered, and the solid was recrystallized from methanol to give the title product (0.20 g, 37%). 1H NMR (400 MHz, DMSO-d6): δ 11.46 (1H, s), 9.15–9.22 (2H, m), 9.02 (1H, s), 8.64 (1H, d, J=8 Hz), 7.15–7.96 (6H, m), 6.06 (2H, s). HRMS (M+H)+ found: 354.1062. Calcd for C19H14F2N3O2FCl: 354.1054.

Provenance & Evidence