2-Chloro-6-nitrotoluene → 3-Chloro-2-methylaniline

Participants

Reaction Conditions

Reaction Steps

To a mixed solution of 150 g of stannous chloride and 200 ml of concentrated sulfuric acid under ice-cooling is added 29 g of 2-chloro-6-nitrotoluene. Then, the solution is heated at 100° C. for 1 hour, resulting in white crystals. The crystals are recovered by filtration and dissolved in a mixed solution of 400 ml of water and 50 ml of a 40% NaOH solution, followed by extracting with 500 ml of chloroform. After washing the extract with 400 ml of water, the chloroform layer is dried over anhydrous magnesium sulfate, and the solvent is distilled off under reduced pressure for concentration. Distillation of the resultant residue yields 23 g of 2-methyl-3-chloroaniline as the fraction of 115°-116° C./10 mmHg.

Provenance & Evidence