Реакция #60515

Уравнение реакции

1-fluoro-3-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene

ammonium chloride

water

→

title compound

Выход 31.5%

3-Fluoro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine

Выход 31.5%

Растворители

ethanol

Условия реакции

Обработка

1. 1
   ФильтрацияThe reaction mixture was filtered
2. 2
   Концентрированиеthe filtrate was concentrated under reduced pressure
3. 3
   workup.ADDITIONEthyl acetate and water were added to the obtained residue and extraction
4. 4
   ПромывкаThe separated organic layer was washed with brine
5. 5
   Сушкаdried over anhydrous sodium sulfate
6. 6
   ФильтрацияThe desiccant was filtered off
7. 7
   Концентрированиеthe filtrate was concentrated under reduced pressure
8. 8
   ДругоеThe resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane)

Методика

To a solution of 1-fluoro-3-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene (2.25 g, 8.11 mmol) produced in Example (97b) in ethanol (45 mL) were added ammonium chloride (150 mg, 2.8 mmol), water (15 mL) and iron powder (1.6 g, 28.65 mmol), followed by stirring for 2 hours at an external temperature of 90° C. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. Ethyl acetate and water were added to the obtained residue and extraction was performed with ethyl acetate. The separated organic layer was washed with brine and then dried over anhydrous sodium sulfate. The desiccant was filtered off and the filtrate was concentrated under reduced pressure. The resultant residue was purified by NH silica gel column chromatography (ethyl acetate/heptane) to give 632 mg of the title compound as a light yellow oil.

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