Hydrochloric Acid → 2-Nitro-5-(4-oxo-4H-pyridin-1-yl)-aniline

Participants

Reaction Conditions

Reaction Steps

First, 8.628 g of 5-chloro-2-nitroaniline, 7.161 g of 4-hydroxypyridine, and 4.892 g of powdered potassium hydroxide were added to 60 ml of dry dimethylsulfoxide The mixture thus obtained was stirred at 130° C. for 3 hours in a nitrogen atmosphere. Then, 200 ml of ice water was added to the reaction mixture and neutralized with 4N hydrochloric acid. The resultant solution was stirred for 30 minutes, giving a precipitate. The precipitate was filtered and washed with water. The precipitate was subjected to silica gel column chromatography, and fractions eluted with 20% methanol in methylene chloride were collected. The collected fractions were combined and evaporated. The residue was recrystallized in methanol to give 11.868 g of yellowish orange crystals of 2-nitro-5-(4-oxo-4H-pyridin-1-yl)-aniline.

Provenance & Evidence