4-Nitroaniline → Methyl-3-(p-nitrophenylcarbamoyl)benzoate

Participants

Reaction Steps

In a 1-liter 3-necked flask fitted with an inlet tube for nitrogen, a magnetic stirrer, a dropping funnel and a thermometer there were introduced 76 g (0.5 moles) of p-nitroaniline in 600 ml of dimethylacetamide and 80 ml of pyridine. (Both solvents had previously been dried over a molecular sieve 3A). Over a period of 45 minutes 99.2 g (0.5 moles) of 3-carbomethoxybenzoyl chloride in 100 ml of dimethylacetamide were added with stirring and cooling, care being taken that the temperature did not rise to above 15° C. In the process a yellow precipitate was formed. After all the ingredients had been added, stirring was continued for 1 more hour at 20° C. The reaction mixture was poured into 2 l of ice water, filtered, washed 6 times with water and finally with methanol. After drying at 70° C. and a pressure of 133 Pa 146 g of the envisaged product were obtained in a yield of 97%. The melting point was 206°-207.6° C. In an analogous manner there were prepared:

Provenance & Evidence