Triethylamine → 3-(Azidocarbonyl)-2-chloropyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-chloronicotinic acid (1.0 g, 6.35 mmol) in a mixture of acetone (14 mL) and water (6 mL) was added triethylamine (0.97 mL, 6.98 mmol). The mixture was cooled to 0° C. in a ice-bath. Ethylchloroformate (1.03 g, 9.5 mmol) was then added and the resulting mixture was stirred for 1.0 hour at 0° C. To the mixture was added sodium azide (0.70 g, 10.8 mmol), and the mixture was stirred for another 3 hours. The mixture was concentrated, the residue was diluted with dichloromethane and washed with water. The organic layer was dried over MgSO4 and concentrated to give desired product (550 mg, 48%). 1HNMR (CDCl3) (δ) 8.57 (d, 1H), 8.22 (d, 1H), 7.37 (t, 1H).

Provenance & Evidence