Sodium Azide → 3-Azido-4-methylbenzoic acid

Participants

Reaction Conditions

Reaction Steps

3-Amino-4-methyl benzoic acid (2.28 g, 15.1 mmol) was suspended in 65 mL of 2N HCl and chilled to 0° C. A chilled solution of 1.25 g (18.1 mmol) of NaNO2 in 5 mL of water was added slowly, and the solution was stirred for 30 min. The mixture was filtered through a plug of diatomaceous earth, and then returned to a 0° C. bath where 1.08 g (16.6 mmol) of NaN3 dissolved in about 5 mL of water was slowly added. Gas evolved immediately, and a precipitate formed. The precipitate was filtered, washed with water, and dried under a stream of air to provide 2.34 g (13.4 mmol; 88%) of Compound 2 as a white solid.

Provenance & Evidence