Reacción #812449

Ecuación de reacción

potassium hydroxide

N-(3,4-dimethylphenyl)acetamide

potassium carbonate

4-bromobiphenyl

→

N-(3,4-dimethylphenyl)-4-biphenylamine

Disolventes

—

denatured alcohol

tridecane

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroIn a 1 liter round bottomed flask equipped with a mechanical stirrer
2. 2
   Otrofitted with a Dean-Stark trap under a reflux condenser
3. 3
   OtroThe resulting reaction mixture
4. 4
   Temperaturato cool to 80° C.
5. 5
   Temperaturato reflux for 3 hours
6. 6
   TemperaturaThe reaction mixture was then cooled to room temperature, about 25° C.
7. 7
   Otroprecipitation
8. 8
   FiltraciónThe intermediate product was filtered
9. 9
   Lavadowashed liberally with deionized water
10. 10
    Otrowater was removed by azeotropic distillation
11. 11
    workup.ADDITIONby adding 45 grams of Alcoa CG-20 alumina
12. 12
    Temperaturaat reflux for 3 hours
13. 13
    OtroThe intermediate product was then recrystallized
14. 14
    Temperaturaon cooling to room temperature
15. 15
    Otrowas isolated by vacuum filtration
16. 16
    OtroAn off-white powder of weight 202.2 grams (74 percent) resulted, suitable for use in the following Example II reaction

Procedimiento

In a 1 liter round bottomed flask equipped with a mechanical stirrer and fitted with a Dean-Stark trap under a reflux condenser were placed 166.48 grams (1.02 mole) of N-(3,4-dimethylphenyl)acetamide, 233.1 gram (1.02 mole) of 4-bromobiphenyl, 7.5 grams (0.03 mole) of cupric sulfate pentahydrate, 165.86 grams (1.2 moles) of potassium carbonate, and 20 milliliters of tridecane solvent. The resulting reaction mixture was then heated rapidly over a period of about thirty minutes to a temperature of 230° C. (Centigrade) and allowed to proceed for 14 hours at this temperature. The reaction was then allowed to cool to 80° C. and 800 milliliters of denatured alcohol and 165.5 grams (2.95 moles) of flake potassium hydroxide were added. The reaction mixture was then reheated to reflux for 3 hours to complete the amide hydrolysis. The reaction mixture was then cooled to room temperature, about 25° C., and added rapidly to 2 liters of deionized water to provoke precipitation. The intermediate product was filtered and washed liberally with deionized water. The resulting wet cake was taken up in 1 liter of hot isooctane and water was removed by azeotropic distillation. The intermediate product was decolorized by adding 45 grams of Alcoa CG-20 alumina and stirring at reflux for 3 hours. The intermediate product was then recrystallized on cooling to room temperature and was isolated by vacuum filtration. An off-white powder of weight 202.2 grams (74 percent) resulted, suitable for use in the following Example II reaction. Purity of this intermediate product was about 97 to about 99.5 percent as determined by high performance liquid chromatography.

Fuente