O-Toluidine → 2,2,2'-Trimethylpropionanilide

Participants

Reaction Steps

To a solution of o-tolylamine (21 g, 0.20 mol) and Et3N (22 g, 0.22 mol) in CH2Cl2 was added 2,2-dimethyl-propionyl chloride (25 g, 0.21 mol) at 10° C. After addition, the mixture was stirred overnight at room temperature. The mixture was washed with aq. HCl (5%, 80 mL), saturated aq. NaHCO3 and brine. The organic layer was dried over Na2SO4 and concentrated under vacuum to give N-o-tolylpivalamide (35 g, 91%). 1H NMR (300 MHz, CDCl3) δ 7.88 (d, J=7.2 Hz, 1 H), 7.15-7.25 (m, 2 H), 7.05 (t, J=7.2 Hz, 1 H), 2.26 (s, 3 H), 1.34 (s, 9 H).

Provenance & Evidence