Water → 2,2-dimethyl-N-(5-nitropyridin-2-yl)propanamide

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Reaction Steps

5-nitropyridin-2-amine (0.5 g, 3.59 mmol) was slurried in DCM (12 ml). TEA (2.5 ml, 18 mmol) and DMAP (88 mg, 0.72 mmol) were added. 2,2-dimethylpropanoyl chloride was added prop wise and the mixture stirred at RT overnight. The mixture was diluted into water (30 ml):saturated sodium bicarbonate (aq, 10 ml), extracted with DCM (3×30 ml), the organic fractions combined, washed with brine, dried over Na2SO4, filtered, and the volatiles removed in vacuum. The material was purified by chromatography on SiO2 eluting with 10% acetone: hexanes to give the titled compound.

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