Reaction #3231

Reaction equation

4-methyl-2-nitroaniline

chlorine

→

title compound

Yield 25.0%

2-Chloro-4-methyl-6-nitroaniline

Yield 25.0%

Solvents

chloroform

chloroform

Conditions

Workup

1. 1
   Temperaturewhile maintaining the reaction mixture temperature below 30° C
2. 2
   Washwashed with aqueous sodium bicarbonate
3. 3
   ConcentrationThe organic phase was then concentrated
4. 4
   Otherthe residue chromatographed (eluant: hexane/diethyl ether; 9/1) over silica gel

Procedure

To a stirred solution of 4-methyl-2-nitroaniline (19.69 g, 129.4 mM) in chloroform (200 mL) under a nitrogen atmosphere was added dropwise a solution of chlorine (10.15 g, 285.9 mM) in chloroform (100 mL) while maintaining the reaction mixture temperature below 30° C. The reaction mixture was stirred for 3 days and then washed with aqueous sodium bicarbonate. The organic phase was then concentrated and the residue chromatographed (eluant: hexane/diethyl ether; 9/1) over silica gel to provide (6.03 g, 25%) the title compound as an orange crystalline solid, mp 68.5°-69.5° C.; MS(CI): 187 (M+H).

Source