Acetone → 2-(4,5-dihydro-1H-imidazol-2-yl)pyridine

Participants

Reaction Steps

8.3 Grams (80 mM) of 2-cyanopyridine was dissolved in 80 ml absolute ethanol and placed in a 250 ml round-bottom flask. 20 Ml of hydrazine hydrate (90%) in 30 ml of ethanol was added to it in one portion and stirred at room temperature for 5 hours. TLC (15:35 chloroform/n-pentane on silica gel) showed no starting material. The reaction mixture was then treated with 25 ml acetone and stirred for 1 hour. It was concentrated to about 100 ml, when a yellow precipitate formed. The latter was washed with water and filtered, to give 9.5 g (65%) yellow crystals. They were dried in vacuo overnight, after which the melting point was 95°-97° C.

Provenance & Evidence