Ammonium Chloride → 2-(4,4-Dimethylcyclohex-1-enyl)-5-methoxyphenylamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-(4,4-dimethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene (3.5 g, 13.4 mmol) prepared in Example (1c) in ethanol (30 mL) were added a solution (5 mL) of aqueous ammonium chloride (2.9 g, 54 mmol) and iron powder (1.5 g, 26.8 mmol), and the mixture was stirred at an external temperature of 90° C. for 1 hour and 30 minutes. The reaction mixture was passed through Celite, brine was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the desiccant was filtered off. The filtrate was concentrated under reduced pressure to give 3.35 g of the title compound as a yellow oil.

Provenance & Evidence