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To 50 ml. of tert-butanol, there was added potassium tert-butoxide (0.06 mole) and 2-chloro-5-nitropyridine (0.05 mole). A white solid precipitated. The reaction mixture was heated to about 60° for 4 hours. Excess ammonium chloride was added to neutralize excess potassium tert-butoxide. Solvent was removed by evaporation, and the residue was taken up in chloroform, separated, washed with water, dried over magnesium sulfate, and chromatographed on silica gel with a 50:50 mixture of ethyl acetate:toluene. The structure was confirmed by NMR spectroscopy.

1. customA white solid precipitated
2. temperatureThe reaction mixture was heated to about 60° for 4 hours
3. additionExcess ammonium chloride was added
4. customSolvent was removed by evaporation
5. customseparated
6. washwashed with water
7. dry with materialdried over magnesium sulfate
8. customchromatographed on silica gel with a 50:50 mixture of ethyl acetate