3,4-Dimethylaniline → N-(1-ethylpropyl)-3,4-dimethylaniline

Participants

Reaction Conditions

Reaction Steps

A Parr hydrogenation apparatus was charged with 1.2 grams 5% platinum on carbon, 0.62 g 3,5-dihydroxybenzoic acid (pKa=1.92), 24.2 grams 3,4-xylidine and 28.0 grams diethyl ketone. The mixture heated to 70° C. and hydrogenated at 35-60 psig. The mixture was cooled, filtered, the filter cake washed with methanol, and the organic phase (87.7 g) analyzed by gas-liquid chromatography. Thus, 28.7 g of N-3-pentyl-3,4-xylidine was obtained, corresponding to a yield of 75.1%.

Provenance & Evidence