5-CHLORO-4-METHYL-2-NITROANILINE

7149-78-2

7149-80-6

(b) Preparation of the intermediate compound 5-chloro-4-methyl-2-nitroaniline: Sodium ethoxide (8.27 g, 45.9 mmol) was dissolved in ethanol (10 mL) to prepare a sodium ethoxide solution. The solution was slowly added to a solution of ethanol (10 mL) containing N-(2-nitro-4-methyl-5-chlorophenyl)acetamide (7.0 g, 30.6 mmol) with stirring at room temperature. After 1 hour of reaction, the reaction mixture was poured into water (100 mL) and precipitate was precipitated. The precipitate was collected by filtration and washed with a mixture of isopropanol and n-hexane (1:3, 10 mL) followed by n-hexane (10 mL) to give 5.71 g (85% yield) of 5-chloro-4-methyl-2-nitroaniline. Mass spectrometry (MS) showed a m/z of 187.0 (M + 1).