Water → 2,2-Dimethyl-N-(4-Methyl-2-pyridyl)propionamide

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Reaction Steps

4-Methyl-pyridin-2-ylamine (30 g, 0.28 mol) was dissolved in DCM (300 mL) and treated with TEA (41 mL) followed by trimethylacetyl chloride (38 mL) via a dropping funnel over 30 min. The mixture was allowed to stir overnight at RT, then poured into a separatory funnel with water (100 mL) and satd. aq. NaHCO3 (75 mL). The organic layer was extracted, washed with satd. aq. NaHCO3 (75 mL), dried over Na2SO4, and concentrated to give solid 2,2-dimethyl-N-(4-methyl-pyridin-2-yl)-propionamide (42 g, 0.22 mol). 1H NMR (CDCl3) δ 8.09 (m, 2 H), 7.93 (br s, 1 H), 6.83 (m, 1 H), 2.33 (s, 3H), 1.29 (s, 9H).

Provenance & Evidence