Phthalimide → 2-(Quinolin-6-ylmethyl)isoindoline-1,3-dione

Participants

Reaction Conditions

Reaction Steps

To a solution of isoindoline-1,3-dione (6.47 g, 44.0 mmol) and triphenylphosphine (11.53 g, 44.0 mmol) in THF (70 mL) at a 0° C., was added a solution of quinolin-6-ylmethanol (7 g, 44.0 mmol) in THF (30 mL) and (E)-diisopropyl diazene-1,2-dicarboxylate (8.89 g, 44.0 mmol) dropwise over a period of 30 min. The mixture was then heated to 30° C. for 20 h. The reaction was cooled to rt and concentrated in vacuo. The resulting residue was purified by Analogix silica gel with gradient hexanes:EtOAc to provide 2-(quinolin-6-ylmethyl)isoindoline-1,3-dione (12.04 g) in 95% yield. LCMS (method A): [MH]+=2.99, tR=4.89 min.

Provenance & Evidence