Phthalimide → HCID 89535922, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of (2-(thiazol-2-yl)phenyl)methanol (0.95 g, 5.1 mmol) in THF (15 mL) was added phthalimide (1.12 g, 7.65 mmol), triphenylphosphine (2.0 g, 7.65 mmol). The mixture was cooled in an ice-water bath and diisopropyl azodicarboxylate (3.1 g, 15.3 mmol) was added dropwise. After the addition, the mixture was stirred at 0° C. for 30 min, and at rt for 18 h. The mixture was then filtered and the filtrate was evaporated. The residue was purified by column chromatography to yield 2-(2-(thiazol-2-yl)benzyl)isoindoline-1,3-dione (1.1 g) as a white solid. To a stirred solution of 2-(2-(thiazol-2-yl)benzyl)isoindoline-1,3-dione (400 mg, 1.25 mmol) in ethanol (10 mL) was added dropwise hydrazine hydrate (160 mg, 3.1 mmol). The mixture was heated at 70° C. for 1 h. After cooling to rt, the mixture was filtered, and the filtrate was evaporated. The residue was purified by column chromatography to yield (2-(thiazol-2-yl)phenyl)methanamine (190 mg) as a white solid.

Provenance & Evidence