Sodium Cyanide → 1-Acetylindoline-5-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 1-(5-aminoindolin-1-yl)ethanone (Aldrich, 865 mg; 4.91 mmol) in HCl (2.1 M, 2.95 mL) was treated with sodium nitrite (358 mg; 5.18 mmol) and the mixture was stirred at 0° C. for 3 hours. The solution was neutralized with sodium carbonate (3.12 g; 29.43 mmol) and the resulting mixture was added to a suspension of sodium cyanide (519 mg; 10.6 mmol) and copper cyanide (467 mg; 5.21 mmol) in water (4 mL) at 0° C. The resulting suspension was heated to 50° C., stirred for 30 minutes, cooled to 0° C. and the precipitated solid was collected by filtration. The collected solid was recrystallised from aqueous acetonitrile to give the title compound as a brown solid. 1H NMR: (DMSO-d6, 400 MHz) δ 8.16 (1H, d, J=8.3 Hz), 7.72-7.62 (2H, m), 4.23-4.11 (2H, m), 2.54 (3H, t, J=2.1 Hz), 2.23 (3H, s).

Provenance & Evidence