Sodium Hydroxide → 3-amino-6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-nitro-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one (10.0 g, 48.73 mmol), tin(II) chloride dihydrate (49.48 g, 219.3 mmol) and ethanol (200 ml) was stirred at 70° C. for 2 hours. The reaction mixture was poured into ice water, adjusted to pH 10 with sodium hydroxide, and then extracted with toluene. The extract solution was washed with water and a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=1/2) to obtain 8.08 g of 3-amino-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one.

Provenance & Evidence