Hydroxyamine hydrochloride → N'-Hydroxy-2-oxoindoline-5-carboxamidine

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-cyanooxindole (5.00 g, 32 mmol) (commercially available from the Combi-Blocks Catalog (Order Number IN-0073), hydroxylamine hydrochloride (4.4 g, 63 mmol), and sodium bicarbonate (11 g, 126 mmol) in 50 mL anhydrous MeOH was heated to 65° C. After 12 hours, the reaction was complete. The mixture was cooled and the suspension was filtered. The resulting solid was washed with 50 mL MeOH. The solid was transferred into a 500 mL round bottom flask and 200 mL distilled water was added. The resulting suspension was sonicated for 5 minutes. Filtration gave the desired compound as an off white solid (5.3 g, 88%). MS (API-ES) m/z (%): 192.0 (100%, M++H).

Provenance & Evidence