Hydrochloric Acid → 2-Amino-5-(diethylamino)toluene

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Reaction Steps

81.5 g of N,N-diethyl-m-toluidine is initially introduced into a stirred flask with 46 ml of hydrochloric acid in 400 ml of water, the reaction mixture is cooled to 0° and gaseous methyl nitrite is passed in, while stirring and cooling. When the introduction of methyl nitrite has ended, the reaction mixture is brought to room temperature, the excess of nitrite is removed in the customary manner by adding urea and the residual gases are removed by applying reduced pressure. The entire reaction mixture is then passed to the catalytic hydrogenation to give 4N,4N-diethyl-2-methyl-p-phenylenediamine without the N,N-diethyl-3-methyl-4-nitroso-aniline formed being isolated. When the hydrogenation has ended, 4N,4N-diethyl-2-methyl-p-phenylenediamine hydrochloride is isolated by precipitation with ethanol. M.p. 268°-272°.

Provenance & Evidence