Pyridinium chloride → 6-chloro-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-benzyl-6-chloro-2,9,10,11-tetrahydro-8,10a -methanoazuleno[2,1-e]indazol-7(8H)-one (0.622 g, 1.66 mmol) and pyridine hydrochloride (10 g, 87 mmol) was heated to 195° C. After 2.5 hours the reaction mixture was allowed to cool to room temperature and was partitioned between EtOAc and water. The organic phase was washed successively with water (3×), 1N aqueous HCl, water and brine and dried over MgSO4. The solvent was evaporated under reduced pressure and the residue was chromatographed on silica gel (elution with 15:85 to 80:20 EtOAc/hexanes) to yield 6-chloro-3,9,10,11-tetrahydro-8,10a-methanoazuleno[2,1-e]indazol-7(8H)-one as a solid.

Provenance & Evidence