4-Aminobenzoic Acid → 4-Azidobenzoic acid

Participants

Reaction Conditions

Reaction Steps

4-aminobenzoic acid (500 mg, 3.65 mmol) was dissolved in 2.5 mL of water and concentrated sulfuric acid (98%, 0.75 mL) and additional water (0.75 mL) were added. The suspension was cooled to 0° C. and a solution of NaNO2 (265 mg, 3.84 mmol) in 0.75 mL of water was added under constant stirring. Sodium azide (293 mg, 4.5 mmol) was added to the brown solution. After additional 15 min of stirring at 0° C. the precipitate was filtered and washed several times with water. The solid was dried to afford 4-azidobenzoic acid (594 mg, 3.64 mmol, 100%) as a white solid. 1H NMR (CD3OD, 500 MHz) δ (ppm): 7.13 (dd, J=1.9, 8.6 Hz, 2H), 8.02 (dd, J=1.9, 8.6 Hz, 2H).

Provenance & Evidence