Phenazopyridine hydrochloride → Phenazopyridine

Participants

Reaction Steps

To a solution of 27.6 grams (200 mmol) of potassium carbonate in 200 mL of water was added 20.0 grams (80 mmol) of phenazopyridine hydrochloride followed by 200 mL of ethyl acetate. The mixture was stirred at room temperature for 30 minutes. The layers were separated and the aqueous layer was extracted one time with 100 mL of ethyl acetate. The ethyl acetate layer was dried over sodium sulfate, and filtered. The filtrate was concentrated under diminished pressure and the product was dried under vacuum at room temperature to give an orange solid: yield 15.1 grams (92%). 1H NMR (300 MHz, CDCl3) δ 4.80 (br s, 4H), 6.06 (d, 1H), 7.34 (m, 1H), 7.48 (m, 2H), 7.76 (m, 2H), and 7.93 (d, 1H).

Provenance & Evidence