3-Aminopyridine → 3-Azidopyridine

Participants

Reaction Steps

Sodium azide (1.5 g) dissolved in 5 ml of water was dropped into a solution of 2.0 g of 3-aminopyridine in 15 ml of 10% hydrochloric acid under cooling with ice. After the reaction solution was stirred for 20 minutes under cooling with ice, 1.8 g of sodium nitrite dissolved in 5 ml of water was dropped in the reaction solution. After temperature of the reaction solution was raised up to room temperature, it was stirred for 1 hour. The reaction solution was diluted with chloroform, washed with water and then with a saturated saline solution and dried over sodium sulfate. The solvent was evaporated in vacuo to give 2.5 g of the title crude compound as a brown oily substance.

Provenance & Evidence