Phthalic Anhydride → HCID 19595161, compound

Participants

Reaction Steps

To a stirred solution of phthalic anhydride (1.76 g) in acetic acid (45 ml), 3-fluoro-4-hydrazinopyridine (1.52 g) was added. The reaction mixture was heated under reflux for 1 hr and concentrated in vacuo to give 3.88 g of 2-(3-fluoro-pyridin-4-ylamino)isoindole-1,3-dione. To a stirred solution of 2-(3-fluoropyridin-4-ylamino)isoindole-1,3-dione (3.88 g) in tetrahydrofuran (125 ml) at 0° C., lithium aluminum hydride (2.86 g) was added. The reaction mixture was allowed to warm to ambient temperature and was stirred for 1 day. Sodium sulfate decahydrate was added, and the mixture was filtered. The filtrate was concentrated in vacuo. The residue was chromatographed on a silica gel eluting with ethyl acetate. The appropriate fractions were collected and concentrated to yield 1.28 g (37%) of product free base. A portion of the free base was dissolved in methanol, and ethereal hydrogen chloride was added. The precipitate was collected and recrystallized from methanol to yield 0.200 g of product, mp 200-202° C.

Provenance & Evidence