Benzamide → 4-Nitroaniline

Participants

Reaction Conditions

Reaction Steps

A 100 ml three-neck reactor equipped with a condenser and a thermometer was filled with 7.32 g (60 mmol) of benzamide, 1.50 g of potassium carbonate, 3.96 g (60 mmol) of potassium hydroxide, 0.3034 g of pyrene, and 25 g of DMSO. Next, the resulting mixture was stirred under oxygen, and then heated to 90° C. Once the reaction temperature reached 90° C., a mixed solution of 2.48 g (20 mmol) of nitrobenzene and 5 g of DMSO was slowly added dropwise over a period of time of 5 to 10 minutes via a syringe. After reacting for 2 hours, a sample was taken out, and dissolved in 2.5 ml of ethyl acetate. Then, moisture of the resulting solution was removed with magnesium sulfate (H2SO4). A quantitative analysis of the product by GC has indicated that 4-nitrosoaniline and 4-nitroaniline were obtained in yields of 14 mole % and 1 mole %, respectively, based on nitrobenzene, and an intermediate N-(4-nitrophenyl)benzamide was also obtained. For the identification of a production of N-(4-nitrophenyl)benzamide, the reaction solution was treated with hexane, added with 5 g of water and 30 g of DMSO, and then left to react at a temperature of 80 to 90° C. for 8 hours. After that, a sample was taken out, and dissolved in 2.5 ml of ethyl acetate. Then, moisture in the resulting solution was removed with magnesium sulfate (H2SO4). A quantitative analysis of the resulting material has shown that 4-nitroaniline was obtained in an yield of 26 mole % based on nitrobenzene.

Provenance & Evidence