反应详情

The reaction sequence set out in FIG. 4 is as follows: 3-chloro-2-methylacetanilide was prepared from 3-chloro-2-methylaniline via acetylation of the aniline with acetic anhydride in an aqueous methanol solution. A mixture of chloro-methylnitro-acetanilide isomers was thereafter formed by nitration of the acetanilide with sulfuric and nitric acid. The 3-chloro-2-methyl4-nitro isomer was removed by precipitation after addition of potassium hydroxide to the mixture of isomer in ethanol. The 3-chloro-2-methyl-6-nitroacetanilide was heated to reflux in an aqueous sodium hydroxide solution. The solid that formed was 3-chloro-2-methyl-6-nitroaniline. Reaction with a solution of stannous chloride in hydrochloric acid yielded a precipitate of 4-chloro-3-methyl-1,2-benzenediamine. Reaction with sodium nitrite in acetic acid yielded a solid 5-chloro4-methylbenzotriazole.

1. customThe 3-chloro-2-methyl4-nitro isomer was removed by precipitation
2. additionafter addition of potassium hydroxide
3. additionto the mixture of isomer in ethanol
4. temperatureThe 3-chloro-2-methyl-6-nitroacetanilide was heated
5. temperatureto reflux in an aqueous sodium hydroxide solution
6. customThe solid that formed