Реакция #47836

Уравнение реакции

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

Выход 75.6%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   Температураrefluxed for 3 hrs
2. 2
   ПромывкаThe resulting mixture washed with saturated sodium bicarbonate
3. 3
   Экстракцияextracted with ethyl acetate
4. 4
   ДругоеThe organic layer was separated
5. 5
   Сушкаdried over anhydrous MgSO4
6. 6
   Концентрированиеconcentrated under a reduced pressure
7. 7
   ДругоеThe resulting residue was purified by flash chromatography

Методика

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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