Butanedione → HCID 178474136, compound

Participants

Reaction Steps

To a solution of N-(3-carbamimidoyl-phenyl)-acetamide hydrochloride (9.75 g, 45.6 mmol, 1.0 equiv; [CAS RN 521269-31-8], prepared according to WO 03/037 327 A1 (Hoffmann-La Roche A G)) in 2-propanol (180 mL) was added butane-2,3-dione (4.91 g, 57.0 mmol, 1.25 equiv). After heating to reflux for 20 h, the solvent was removed by evaporation under reduced pressure, water (20 mL) and 4 M HCl (40 mL) were added and the reaction mixture heated to reflux for an additional time period of 16 h. The reaction mixture was cooled down to rt, concentrated by evaporation under reduced pressure and the crude reaction product purified with column chromatography on silica eluting with dichloromethane/methanol (95:5) to give 2.6 g (23%) of the title compound. MS (ISP): 246.2 [M+H]+.

Provenance & Evidence