Uses
N-(2,6-Dichlorophenyl)aniline is an analog of Diclofenac (D436450), a nonsteroidal anti-inflammatory compound an decycloxygenase (COX) inhibitor.
Synthesis
The general procedure for the synthesis of 2,6-dichloro-N-phenylaniline from the compound (CAS:146607-19-4) was as follows: compound II (272 g, 0.92 mol) was added to a dry four-necked flask with toluene (800 g, 8.7 mol) and heated to 90 °C. Sodium hydroxide (total 14.8 g, 0.37 mol) was added in three portions under stirring, followed by refluxing the reaction mixture for 3 hours. After completion of the reaction, the mixture was cooled to below 80°C. 184 mL of distilled water was added to the reaction flask and the temperature was raised to 90 °C with continuous stirring for 1 hour. The reaction solution was transferred to a dispensing funnel and washed sequentially by adding 46 mL of water and 28 mL of hydrochloric acid. The washed organic phase was transferred to a distillation flask and toluene was removed by distillation under reduced pressure. Finally 203.4 g of light yellow solid product was obtained as N-(2,6-dichlorophenyl)aniline (Compound III) in 93% yield.
