Water → 4-(2,2,2-Trimethylacetamido)pyridine

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Following procedures generally taught in J. A. Turner, J. Org. Chem. 1983, 48, 3401-3408, a solution of pivaloyl chloride (13.5 mL, 110 mmol) in CH2Cl2 (20 mL) was slowly added to an ice-cold solution of 4-aminopyridine (9.41 g, 100 mmol) and triethylamine (17.4 mL, 125 mmol) in CH2Cl2 (150 mL). After addition was complete, the resulting mixture was warmed to room temperature and stirred for 2 h. The solution was poured into water, the CH2Cl2 layer was washed with dilute NaHCO3, dried over Na2SO4, and evaporated to leave a light brown solid. Recrystallization from EtOAc/hexanes afforded the product as a white crystal, which was collected by vacuum filtration (13.03 g, 73%). 1H NMR (400 MHz, CDCl3) δ 8.50 (d, J=4.8 Hz, 2 H), 7.50 (d, J=4.8 Hz, 2 H), 7.44 (br s, 1 H), 1.33 (s, 9 H). MS (LR-APCI) calcd. for C10H15N2O (M+H) 179.1; found 179.1.

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