Abstract
3, 5-Dinitro-4-cyanopyridine was prepared from 3, 5-dinitro-4-chloropyridine by heating it with cuprous cyanide, directly or in nitrobenzene, as platelet crystals of m.p. 140°, with a maximum yield of 45%. Treatment of 4-hydroxy-3, 5-dinitro-α-picoline 1-oxide with phosphorus trichloride in ethyl acetate gave 3, 5-dinitro-4-hydroxy-α-picoline in 87% yield, as pale yellow plates, m.p. 269° (decomp.). Further heating of the latter with phosphoryl chloride gave 3, 5-dinitro-4-chloro-α-picoline in 73% yield as colorless prisms, m.p. 108°. The latter was easily sublimable and its heating with cuprous cyanide failed to yield 4-cyano derivative, resulting in the recovery of 70-90% of the starting material.
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