Hydrochloric Acid → 2-(2-Oxo-2-(pyridin-3-YL)ethyl)isoindoline-1,3-dione

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Reaction Steps

A solution of bromomethylpyridin-3-yl ketone (4.55 g, 16.2 mmol) and potassium phthalimide (6.0 g, 32.4 mmol) in DMF (50 mL) was stirred for 3 days at rt before the added to diluted brine (500 ml, 1:1). The solution was made acidic (pH 2) with diluted hydrochloric acid (1M) before washed with ethyl acetate (2×100 ml). The aqueous layer was then made alkaline (pH 12) again with sodium hydroxide solution (2 M) and extracted with DCM (4×200 ml). The extracts were combined and dried (MgSO4) before concentrated in vacuo. Recrystallisation from methanol (2×) allows to remove crystalline phthalimide and to enrich the title compound in the mother liquer. The crude product was used in Preparation 98 without further purification. δH (d6 DMSO): 5.33 (2H, s), 7.64 (1H, dd), 7.92, 7.97 (4H, 2m), 8.43 (1H, m), 8.88 (1H, m), 9.28 (1H, s); m/z (ES+)=308.13 [M+MeCN +H]+; RT=2.39 min.

Provenance & Evidence