Hydrochloric Acid → alpha-(2-Hydroxy-5-sulfophenylazo)acetoacetanilide

Participants

Reaction Conditions

Reaction Steps

2-Aminophenol-4-sulfonic acid (18 g) was dissolved in aqueous sodium hydroxide (5 g in 200 ml of water). After the addition of sodium nitrite (7 g), the solution was cooled to 10° C. and added to a mixture of concentrated hydrochloric acid (25 ml) and cracked ice (300 g). The diazonium solution was stirred at 0° C. for 15 minutes and then added slowly to a slurry of acetoacetanilide (17 g), potassium carbonate (30 g), pyridine (200 ml) and ice. When the addition was complete, the reaction mixture was stirred at 10° to 20° C. for 1 hour and then acidified with hydrochloric acid. The product was filtered off and dried. Yield: 23 g.

Provenance & Evidence