Hydrochloric Acid → 2-Azido-6-chloropyridine

Participants

Reaction Conditions

Reaction Steps

2-Chloro-6-hydrazinopyridine (3.00 g, 20.90 mmol) was suspended in water (20 mL) and cooled to 0° C. Concentrated HCl (3.00 mL, 36.5 mmol) was added to dissolve the starting material and attain a pH of ˜1. Sodium nitrite (1.73 g, 25.07 mmol) in water (10 mL) was added dropwise. The thick suspension was allowed to warm to room temperature and extracted with CH2Cl2 (2×). The combined organic layers were dried (MgSO4), filtered, and evaporated. The crude residue was purified by flash chromatography (0-10% EtOAc/hexanes) to afford the title compound as a colorless solid.

Provenance & Evidence