Reacción #60447

Ecuación de reacción

ammonium chloride

1-nitro-2-(3,3,4,4-tetramethylcyclopent-1-enyl)benzene

ethanol

ammonium chloride

→

title compound

Rendimiento 85.4%

2-(3,3,4,4-Tetramethylcyclopent-1-enyl)phenylamine

Rendimiento 85.4%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.STIRRINGstirring
2. 2
   workup.WAITwas continued for 12 hours at an external temperature of 75° C
3. 3
   TemperaturaThe reaction mixture was cooled to room temperature
4. 4
   Filtraciónfiltered
5. 5
   ConcentraciónThe filtrate was concentrated under reduced pressure
6. 6
   Otrothe resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane)

Procedimiento

To a mixture of 1-nitro-2-(3,3,4,4-tetramethylcyclopent-1-enyl)benzene (441 mg, 1.8 mmol) produced in Example (54b), ethanol (10 mL) and water (3.3 mL) were added ammonium chloride (48.1 mg, 0.899 mmol) and iron powder (352 mg, 6.3 mmol), followed by stirring for 5 hours at an external temperature of 90° C. After further adding ammonium chloride (9.63 mg, 0.18 mmol) and iron powder (100 mg, 1.8 mmol) to the reaction mixture, stirring was continued for 12 hours at an external temperature of 75° C. The reaction mixture was cooled to room temperature and then filtered. The filtrate was concentrated under reduced pressure, and the resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 331 mg of the title compound as a colorless oil.

Fuente