Ammonia → N-benzyl-6,7-dihydro-2-nitro-5H-benzocyclohepten-7-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 7-benzylamino-3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-ol (6.51 g) and potassium bisulfate (13.0 g) was heated at 210° C. for 20 minutes and suspended in a mixture of dichloromethane (150 ml), water (100 ml), and 28% ammonia solution. The suspension was filtered. The dichloromethane layer was separated, dried over magnesium sulfate, evaporated in vacuo, and chromatographed over silica gel using dichloromethane-methanol as an eluent. The first eluate afforded N-benzyl-6,7-dihydro-2-nitro-5H-benzocyclohepten-7-amine (3.11 g) as a dark brown solid.

Provenance & Evidence