Chlorosuccinimide → 2-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one

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Reaction Steps

A solution of 2-benzyl-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one (0.737 g, 2.17 mmol) in 15 mL of dimethylformamide was heated to 60° C. and N-chlorosuccinimide (0.290 g, 2.17 mmol) was added. After heating for 45 minutes, additional N -chlorosuccinimide (0.074 g, 0.55 mmol) was added. After heating for 55 minutes more, the reaction mixture was cooled to room temperature and partitioned between EtOAc and water. The organic phase was washed with water and brine, dried over MgSO4 and concentrated under vacuum. The residue was purified by chromatography on silica gel (elution with 15:85 to 80:20 EtOAc/hexanes) to yield 2-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one as a white solid.

Provenance & Evidence