Ethanol → 3-Methyl-2-(3,3,5,5-tetramethylcyclohex-1-enyl)phenylamine

Participants

Reaction Conditions

Reaction Steps

A mixture of the 1-methyl-3-nitro-2-(3,3,5,5-tetramethylcyclohex-1-enyl)benzene (1 g, 3.66 mmol) produced in Example (71a), iron powder (631 mg, 11.0 mmol), ammonium chloride (783 mg, 14.6 mmol), ethanol (15 mL), water (6 mL) and dimethylformamide (1 mL) was stirred for 3 hours and 30 minutes at an external temperature of 90° C. under a nitrogen atmosphere. Ethyl acetate and water were added to the reaction mixture, and it was filtered through Celite. The filtrate was then extracted with ethyl acetate. The separated organic layer was washed with water and brine in that order 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/hexane) to give 663 mg of the title compound as a light yellow oil.

Provenance & Evidence