Reacción #60450

Ecuación de reacción

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

hydrogen chloride

ethyl acetate

→

title compound

Rendimiento 74.2%

2-(3,3,4,4-Tetramethylcyclopentyl)phenylamine

Rendimiento 74.2%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   FiltraciónThe reaction mixture was filtered
2. 2
   workup.STIRRINGstirring
3. 3
   workup.WAITwas continued for 13 hours and 30 minutes at room temperature
4. 4
   FiltraciónThe reaction mixture was filtered
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

A mixture of 1-nitro-2-(3,3,4,4-tetramethylcyclopent-1-enyl)benzene (450 mg, 1.83 mmol) produced in Example (54b), 10% palladium on carbon (200 mg, wet) and methanol (40 mL) was stirred for 3 hours and 30 minutes at atmospheric pressure and room temperature under a hydrogen atmosphere. The reaction mixture was filtered, 10% palladium on carbon (200 mg, hydrous) and a 4N solution of hydrogen chloride in ethyl acetate (0.915 mL, 3.66 mmol) were added to the filtrate, and then stirring was continued for 13 hours and 30 minutes at room temperature and atmospheric pressure under a hydrogen atmosphere. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure. The resultant residue was purified by silica gel column chromatography (ethyl acetate/heptane) to give 295 mg of the title compound as a brown oil.

Fuente