Pyridine → 5-Acetylaminonaphthalene-2-sulfonic acid

Participants

Reaction Steps

To 29.3 g (0.13 mol) of 5-amino-2-naphthalenesulfonic Acid (Compound 72) was added 40 mL of pyridine and 26 mL of acetic anhydride. The resulting suspension was allowed to stir at ambient temperature. After 24 hr, the resulting solution was diluted with 60 mL of methanol. Then, a solution of 3.6 g (0.156 mol) of sodium in 100 mL of methanol was added. After a solid precipitate began to form, 200 mL of diethyl ether was added and the suspension allowed to stir. The solid was collected by vacuum filtration and was washed with diethyl ether. This provided 38.9 g (0.11 mol) of the desired product. The product was identified by 1H NMR and mass spectroscopy and purity was assessed by RP-HPLC.

Provenance & Evidence