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

반응식

Cl.[C:2]1([NH:12]N)[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][CH:3]=1.[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1CC=O)([O-:16])=[O:15].Cl.[C:27](O)(=O)[CH3:28]>>[N+:14]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:8]1[CH:9]=[CH:10][C:11]2[C:6]([CH:7]=1)=[CH:5][CH:4]=[C:3]1[C:2]=2[NH:12][CH:28]=[CH:27]1)([O-:16])=[O:15]

참가 물질

반응물 4

HCID 176Acetic Acid3회

HCID 313Hydrochloric Acid

HCID 519949Hydrazine, 1-naphthalenyl-, hydrochloride (1:1)

HCID 108447642-Nitrobenzeneacetaldehyde

생성물 1

HCID 218499067-(2-Nitrophenyl)benz[g]indole수율 32%

실험 절차

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.