Benzoic acid, 3-methyl-2-nitro-, methyl ester → Methyl 3-methylanthranilate

Participants

Reaction Steps

In this example 0.02 mole of 2-methyl-6-methoxycarbonyl-nitrobenzene in 25 ml of acetic acid was added dropwise to a slurry containing 6.5 g of zinc dust suspended in 25 ml of water at 30°-35° C. The resulting exothermic reaction is controlled by maintaining the mixture at about room temperature (about 20°-25° C.) through external cooling. The reaction product mixture was filtered to remove the zinc dust and the filtrate, then washed sequentially with methylene chloride and water, and then extracted with methylene chloride. The extract was washed with an aqueous ammonium hydroxide, then with water and filtered through diatomaceous earth. The filtrate was then dried and evaporated affording 2.7 g of the title product as an oil.

Provenance & Evidence