N,N,2-Trimethylaniline → HCID 178482721, compound

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Reaction Steps

13.4 g of ortho-dimethylaminotoluene (or N,N-dimethyl-o-toluidine) (M=135 g.mol−1; 99 mmol) are diluted in a mixture of 40 ml of hexanes and 20 ml of diethyl ether. At ambient temperature, under nitrogen and with stirring, 40 ml of a solution of butyllithium (2.5M in hexane) are added. After 3 h, 1 equivalent of tBuOK is added in fractions, under argon. The solution is heated and a yellow precipitate appears. The stirring is maintained overnight. The solution is filtered and the yellow precipitate is washed three times with a mixture of hexanes (3×40 ml). After drying under vacuum, the solid is milled and dried again under vacuum overnight. 14.9 g of yellow powder of ortho-dimethylaminobenzyl potassium are obtained (yield=80%). 1H NMR (THF-d8, 22° C.): δ=2.03 and 2.57 (2×1H, s, KCH2—), 2.67 (s, 6H, —NMe2), 5.11 (t, 1H, JH-H=7 Hz, aromatic CH), 6.04 (d, 1H, JH-H=7 Hz, aromatic CH), 6.16 (t, 1H, JH-H=7 Hz, aromatic CH), 6.26 (t, 1H, JH-H=7 Hz, aromatic CH).

Provenance & Evidence