Acetic Acid → 7-(2-Nitrophenyl)benz[g]indole

Beteiligte Stoffe

Reaktionsschritte

A suspension of 4.24 g (22.5 mmol) of 1-naphthylhydrazine hydrochloride in acetic acid (35 ml) was slowly boiled and a solution of 3.4 g (20.6 mmol) of 2-nitrophenylacetaldehyde in acetic acid (15 ml) was dropped thereinto under stirring. After the completion of the dropping, the obtained mixture was heated under reflux for 1 hour. Then 20 ml of a mixture of 1 N hydrochloric acid with acetic acid was further added thereto and the obtained mixture was heated under reflux for additional 1 hour. After distilling off the solvent, the residue was dissolved by adding ethyl acetate thereto. The organic layer was washed successively with an aqueous solution of sodium hydrogencarbonate, water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by silica gel column chromatography to thereby give 1.91 g (yield: 32%) of 7-(2-nitrophenyl)benz[g]indole. Then the obtained product was dissolved in ethyl acetate (60 ml) and 200 mg of platinum (IV) oxide was added thereto. Then catalytic reduction was effected under atmospheric pressure in a hydrogen atmosphere at room temperature to thereby give 1.7 g (yield: 99%) of 7-(2-aminophenyl)benz[g]indole.

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