Potassium Cyanide → HCID 178420123, compound

Participants

Reaction Conditions

Reaction Steps

2-Pyridinecarboxaldehyde (4.76 mL, 50 mmol) and tosylmethyl isocyanide (9.76 g, 50 mmol) were suspended in ethanol (150 mL) at room temperature. A catalytic amount of potassium cyanide (0.33 g) was added and the resulting mixture was stirred for 45 min. The mixture became homogeneous after 5 min. of stirring and then a white suspension appeared. The solid material was collected by filtration and rinsed with diethyl ether. After drying under vacuum the solid was transferred to a sealed tube. A 2M solution of ammonia in methanol (20 mL) was added and the tube was sealed and heated at 125° C. for 24 h. The dark reaction mixture was cooled to room temperature and the solvents removed in vacuo. The residue was purified by silica gel chromatography (20-100% EtOAc/Hexane then 0%-50% MeOH/CH2Cl2) to afford 2-(1H-imidazol-4-yl)pyridine as a dark oil. 1H NMR (500 MHz, CD3OD) δ 8.31 (d, 1H), 7.92 (s, 1H), 7.72-7.63 (m, 3H), 7.54 (s, 1H), 7.07 (m, 1H).

Provenance & Evidence