2-Chloro-5-nitropyridine → 2-Tert-butoxy-5-nitropyridine

Participants

Reaction Steps

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.

Provenance & Evidence