Water → 8-bromo-1,2,5,6-tetrahydro-4H-pyrrolo[3,2,1-ij]quinolin-4-one

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To a solution of 1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one (10.0 g, 55.8 mmol) in 100 ml dry DMF was added dropwise a solution of N-bromosuccinimide (10.4 g, 58.6 mmol) in 150 ml dry DMF at 0° C. The mixture was stirred at 0° C. for 2 h, then 400 ml water was added and the solution was extracted with ethyl acetate (3×150 ml). The organic phase was washed with water (2×200 mL), then dried over MgSO4 and evaporated, affording a yellow solid, which was purified by crystallization from acetone/ether providing pure 8-bromo-1,2,5,6-tetrahydro-pyrrolo[3,2,1-ij]quinolin-4-one (12.8 g, 50.8 mmol, 91%) as pale yellow needles.

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