Trimethyl orthoformate → 5-nitro-2-(1H-tetrazol-1-yl)pyridine

Participants

Reaction Steps

The title compound was synthesized using 5-nitropyridin-2-amine (1 g, 6.97 mmol), sodium azide (0.68 g, 10.5 mmol), trimethylorthoformate (1.2 g, 11.2 mmol) and acetic acid (14 mL) and stirred at room temperature over night. The reaction was heated to 120° C. reflux for 7 hours. The reaction was cooled down to room temperature, concentrated to take off acetic acid. Ice water (50 mL) was added, extracted with ethyl acetate (50 mL), second wash with sodium hydroxide (1N, 20 mL). The organic phase was dried by magnesium sulfate, filtered, concentrated and purified by column chromatography through a 50 gram Biotage SNAP KP-Sil™ silica gel cartridge eluting with 30% ethyl acetate/hexanes to give the title compound as a pale yellow solid.

Provenance & Evidence