1-(2-Hydrazino-4-pyridyl)-1-ethylenedioxyethane → 1-(2-Amino-4-pyridyl)-1-ethylenedioxyethane

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Reaction Steps

A mixture of 9.56 g. (49 mmoles) of 1-(2-hydrazino-4-pyridyl)-1-ethylenedioxyethane and 35 g. of Raney nickel in 150 ml. of absolute ethanol was shaken in a hydrogen atmosphere at an initial pressure of 3 atms. at room temperature for 4 hours. The catalyst was filtered and the filtrate concentrated to give 1-(2-amino-4-pyridyl)-1-ethylenedioxyethane as a white solid, m.p. 123°-126° C. The residual material was dissolved in 60 ml. of 2 N hydrochloric acid and heated at 75° C. for 3 hours. The mixture was cooled, neutralized with sodium bicarbonate and extracted with chloroform (30 ml.×6). The combined extracts were dried and concentrated to give a pale yellow solid, which on recrystallization from toluene gave 5.0 g. (75%) of 1-(2-amino-4-pyridyl)-1-ethanone, m.p. 133°-133.5° C.

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