Potassium Hydroxide → N,N-Diethyl-3-hydroxy-4-amino-1-naphthalenesulfonamide

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Reaction Steps

A mixture of N,N-diethyl-2-phenylnaphth[1,2-d]oxazole-5-sulfonamide (38.1 g, 100 mmol), 20% KOH (140 ml) and ethanol (180 ml) was refluxed for 2 h under nitrogen and the product was extracted with ethyl acetate (3×500 ml). The combined extracts were dried over anhydrous sodium sulfate and the solvent evaporated to give 45 g crude N,N-diethyl-4-amino-3-hydroxy-1-naphthalenesulfonamide as a black sticky oil (50% pure by NMR). An analytical sample was prepared by column chromatography (chloroform) to give pure N,N-diethyl-4-amino-3-hydroxy-1-naphthalenesulfonamide as a glassy material which upon titration with ether gave a black solid, m.p. 120°-122° C.

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