3,4-Dimethylaniline → HCID 9837228, compound

Participants

Reaction Steps

In a 500-ml four-necked flask were charged 56 ml of 1,2,3,4-tetrahydronaphthalene (boiling point: 207° C.) as a solvent and 45.0 g (0.42 mol) of m-toluidine, followed by the addition of 25.6 g (0.23 mol) of anhydrous calcium chloride and 30.8 g (0.23 mol) of anhydrous aluminum chloride under stirring. After stirring at an internal temperature of 100 to 120° C. for 30 minutes under a nitrogen atmosphere, the reaction mixture was added with 50.9 g (0.42 mol) of 3,4-xylidine. The resulting mixture was reacted at an internal temperature of 210 to 220° C. for 3 hours. After cooling, the reaction mixture was added with 126 ml of toluene, followed by charging in 160 g of ice water. The resulting mixture was stirred and then, allowed to stand, whereby a water layer was separated out. The organic layer was washed successively with 150 ml of a 5% aqueous solution of hydrochloric acid, 100 ml of a 5% aqueous solution of sodium bicarbonate and 100 ml of water. From the organic solvent, the distillate at 134 to 135° C. and a vacuum degree of 0.4 to 0.5 Torr was collected, whereby 37.9 g (yield: 42.7%) of the title compound was obtained as a slightly yellow oil. As a result of HPLC. analysis (column: YMC-A-312, detection UV: 280 nm, flow rate: 1.0 ml/min, eluent: acetonitrile/water=8/2), the compound was found to have a purity of 99.3%.

Provenance & Evidence