Hydrochloric Acid → 4-(4-Oxo-4H-pyridin-1-yl)-1,2-phenylenediamine

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Reaction Steps

First, 5.515 g of 2-nitro-5-(4-oxo-4H-pyridin-1-yl)-aniline was added to a suspension containing 7.975 g of iron powder, 20 ml of water, and 78 ml of ethanol, followed by adding 2 ml of 2N hydrochloric acid. The resultant mixture was refluxed by heating for 6 hours. Then, 1.092 g of iron powder and 2 ml of 2N hydrochloric acid were added to the mixture. The resultant mixture was refluxed for another 1 hour. After the reaction, the reaction mixture was hot filtered using celite, and a residue on the celite was thoroughly washed with warm ethanol. The mother liquor and the washings were combined together and concentrated to dryness. The residue thus obtained was subjected to silica gel column chromatography, and fractions eluted with 5% methanol in chloroform were collected. The collected fractions were combined and evaporated. The residue was recrystallized with isopropanol-methanol (1:1) to give 4.137 g of orange crystals of 4-(4-oxo-4H-pyridin-1-yl)-1,2-phenylenediamine.

Provenance & Evidence