反応 #47836

反応方程式

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

収率 75.6%

溶媒

ethanol

反応条件

後処理

1. 1
   温度refluxed for 3 hrs
2. 2
   洗浄The resulting mixture washed with saturated sodium bicarbonate
3. 3
   抽出extracted with ethyl acetate
4. 4
   その他The organic layer was separated
5. 5
   乾燥dried over anhydrous MgSO4
6. 6
   濃縮concentrated under a reduced pressure
7. 7
   その他The resulting residue was purified by flash chromatography

実験手順

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%).

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