Acetone → HCID 178518991, compound

Participants

Reaction Steps

To a stirred solution of isoxazolo[5,4-c]pyridin-3-ol (50.0 g, 367 mmol) in NMP (100 ml) was added benzyl bromide (75.4 g, 441 mmol) dropwise rapidly. The thick solution was stirred for 24 h. The mixture was then added slowly to acetone (1.5 L) with stirring, and the solution was seeded. Stirring was continued at room temperature for 30 min, and then for a further 1 h in an ice/water bath. The mixture was filtered, the residue was washed with acetone and then dried under vacuum to give 6-benzyl-3-hydroxy-isoxazolo[5,4-c]pyridin-6-ium bromide (94.1 g, 83%; HPLC: 91% pure) as a white crystalline solid.

Provenance & Evidence