반응 #47836

반응 방정식

1-Oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile

hydroxylamine hydrochloride

pyridine

→

1-hydroxyimino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile

수율 75.6%

용매

ethanol

반응 조건

후처리

1. 1
   온도refluxed for 3 hrs
2. 2
   세척The resulting mixture washed with saturated sodium bicarbonate
3. 3
   추출extracted with ethyl acetate
4. 4
   기타The organic layer was separated
5. 5
   건조dried over anhydrous MgSO4
6. 6
   농축concentrated under a reduced pressure
7. 7
   기타The resulting residue was purified by flash chromatography

실험 절차

1-Oxo-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile (293 mg, 0.80 mmol) obtained in Example 11 was dissolved in ethanol (20 mL), and hydroxylamine hydrochloride (167 mg, 2.41 mmol) and pyridine (254 mg, 3.21 mmol) were added thereto, refluxed for 3 hrs, and cooled to RT. The resulting mixture washed with saturated sodium bicarbonate, extracted with ethyl acetate. The organic layer was separated, dried over anhydrous MgSO4 and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 230 mg of 1-hydroxyimino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile (yield: 75%). Subsequently, 1-hydroxyimino-3-phenyl-6-(3-phenyl-propoxy)-1H-indene-2-carbonitrile (230 mg, 0.60 mmol) thus obtained was dissolved in methanol (20 mL), and 10%-palladium (230 mg) was added thereto. The mixture was stirred for 15 hrs at RT while providing H2 gas thereto using a balloon, filtered through celite, and concentrated under a reduced pressure. The resulting residue was purified by flash chromatography to obtain 90 mg of the titled compound (yield: 41%).

출처