Methyl iodide → N-allyl-N-methyl-2-methyl-4-nitroaniline

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Reaction Steps

20 g (104 mmol) of N-allyl-2-methyl-4-nitroaniline were dissolved in 600 ml of dimethyl sulfoxide. 41.6 g (1.04 mol) of sodium hydroxide powder were added to the resultant solution, whereupon the solution became deep red. 44.3 g (19.6 ml, 312 mmol) of methyl iodide were added in one portion, and the solution became red-brown. The red-brown solution was stirred at room temperature for from 1 to 2 hours, poured into 3 l of ice water and then extracted three times with 500 ml of dichloromethane in each case. The combined dichloromethane phases were subsequently washed three times with 500 ml of water in each case, dried over sodium sulfate, filtered and evaporated under reduced pressure, to give a brown oil (21.4 g, corresponding to a yield of 99%), which was purified by chromatography on silica gel (eluent: n-hexane/ethyl acetate 15/1), to give N-allyl-N-methyl-2-methyl-4-nitroaniline (compound I-8 according to the invention) in a yield of 19.5 g, corresponding to 90%.

Provenance & Evidence