Reaction #487555

Reaction equation

4′-Chloro-4-ethyl-3-nitrobiphenyl

water

ammonium chloride

→

3-amino-4′-chloro-4-ethylbiphenyl

Yield 75.3%

Solvents

methanol

Conditions

Workup

1. 1
   Temperaturethe mixture is heated
2. 2
   Temperatureto reflux for 1 hour
3. 3
   TemperatureThe reaction mixture is cooled to room temperature
4. 4
   Filtrationfiltered through diatomaceous earth
5. 5
   Otherthe filtrate is evaporated in vacuo
6. 6
   Otherto remove most of the methanol
7. 7
   OtherThe residue is partitioned between ethyl acetate (200 ml) and water
8. 8
   Extractionthe aqueous phase is re-extracted with ethyl acetate (200 ml)
9. 9
   Washwashed with water and brine
10. 10
    Dryingdried over anhydrous magnesium sulfate
11. 11
    Filtrationfiltered
12. 12
    Otherthe filtrate is evaporated in vacuo

Procedure

4′-Chloro-4-ethyl-3-nitrobiphenyl (22.6 g, 0.086 mol) is suspended in methanol (250 ml) and the reaction mixture is stirred at room temperature. Distilled water (100 ml) is added, followed by zinc dust (39.0 g, 0.60 mol) and ammonium chloride (13.8 g, 0.26 mol) and the mixture is heated to reflux for 1 hour. The reaction mixture is cooled to room temperature, filtered through diatomaceous earth and the filtrate is evaporated in vacuo to remove most of the methanol. The residue is partitioned between ethyl acetate (200 ml) and water and the aqueous phase is re-extracted with ethyl acetate (200 ml). The organic extracts are combined, washed with water and brine, dried over anhydrous magnesium sulfate, filtered and the filtrate is evaporated in vacuo to give 3-amino-4′-chloro-4-ethylbiphenyl (15.0 g) as a colourless solid. The product is used directly without further purification in Step 5.

Source