Aniline → 4-Nitrodiphenylamine

Participants

Reaction Conditions

Reaction Steps

93 g of aniline, 3.8 g of 1,8-diazabicyclo[5,4,0]undec-7-ene, 2 g of copper(II)oxide and 40 ml of xylene are heated together to 150° C. for 20 minutes in a water separator. 157.5 g of 4-nitrochlorobenzene, 93 g of aniline and 76 g of calcined sodium carbonate (light) are then added. After 12 hours at 193°-196° C., 10 ml of water have collected in the water separator. The weight ratio of nitrobenzene:4-nitrochlorobenzene:4-nitrodiphenylamine in the reaction mixture is 1.5:2.0:96.5. The reaction mixture is cooled to 95° C. and filtered, and the filter cake is washed with 100 ml of hot xylene. Water is added to the filtrate, and unreacted 4-nitrochlorobenzene and aniline are expelled with steam, the 4-nitrodiphenylamine being obtained as granules. It is isolated by filtration, washed with hot water and dried: 210 g of 4-nitrodiphenylamine, purity (HPLC) 91.3%, yield 89.6 % of theory, relative to p-nitrochlorobenzene employed.

Provenance & Evidence