HCID 58641512, compound → HCID 58641559, compound

Participants

Reaction Steps

A solution of (7-benzenesulfonyl-3-oxo-2,3-dihydro-benzo[1,4]oxazin-4-yl)-acetonitrile (0.234 g., 0.713 mmol) in 2 mL anhydrous THF was warmed to reflux, and borane-methyl sulfide complex (0.5 mL of a 10 M solution, 5 mmol) was added dropwise over 5 minutes. Reflux was continued for 4 hours, and the reaction mixture was concentrated in vacuo. The residue was then dissolved in 2 mL ethanol and ethanolic hydrogen chloride was added (2 mL of a 2 N solution, 4 mmol.) The solution was refluxed for 18 hours then cooled to room temperature, resulting in formation of a precipitate. The solid was filtered and dried under vacuum for 18 hours to give 0.158 g (0.496 mmol, 70%) of 2-(7-benzenesulfonyl-2,3-dihydro-benzo[1,4]oxazin-4-yl)-ethylamine as a yellowish solid. MS: 319 (M+H)+, mp: 261.0-265.1° C. (HCl salt).

Provenance & Evidence