Reaction #60420

Reaction equation

1-(4,4-diethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene

ammonium chloride

→

title compound

Yield 120.8%

2-(4,4-Diethylcyclohex-1-enyl)-5-methoxyphenylamine

Yield 120.8%

Solvents

ethanol

Conditions

Workup

1. 1
   FiltrationThe reaction mixture was passed through Celite for filtration
2. 2
   workup.ADDITIONbrine was added to the filtrate
3. 3
   Extractionthe mixture was extracted with ethyl acetate
4. 4
   DryingThe organic layer was dried over anhydrous magnesium sulfate
5. 5
   Filtrationthe desiccant was filtered off
6. 6
   Concentrationthe filtrate was concentrated under reduced pressure

Procedure

To a solution of 1-(4,4-diethylcyclohex-1-enyl)-4-methoxy-2-nitrobenzene (2.4 g, 8.3 mmol) prepared in Example (6d) in ethanol (20 mL) were added an aqueous solution (5 mL) of ammonium chloride (2.2 g, 41 mmol) and iron powder (1.2 g, 20.7 mmol), and the mixture was stirred at an external temperature of 90° C. for 1 hour. The reaction mixture was passed through Celite for filtration, and then brine was added to the filtrate and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, the desiccant was filtered off, and then the filtrate was concentrated under reduced pressure to give 2.6 g of the title compound as a yellow oil.

Source