Reacción #487555

Ecuación de reacción

4′-Chloro-4-ethyl-3-nitrobiphenyl

water

ammonium chloride

→

3-amino-4′-chloro-4-ethylbiphenyl

Rendimiento 75.3%

Disolventes

methanol

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturathe mixture is heated
2. 2
   Temperaturato reflux for 1 hour
3. 3
   TemperaturaThe reaction mixture is cooled to room temperature
4. 4
   Filtraciónfiltered through diatomaceous earth
5. 5
   Otrothe filtrate is evaporated in vacuo
6. 6
   Otroto remove most of the methanol
7. 7
   OtroThe residue is partitioned between ethyl acetate (200 ml) and water
8. 8
   Extracciónthe aqueous phase is re-extracted with ethyl acetate (200 ml)
9. 9
   Lavadowashed with water and brine
10. 10
    Secadodried over anhydrous magnesium sulfate
11. 11
    Filtraciónfiltered
12. 12
    Otrothe filtrate is evaporated in vacuo

Procedimiento

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.

Fuente