Phosphorus oxychloride → 6-Acetamido-4-chloro-[1,5]naphthyridine-3-carbonitrile

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Reaction Steps

A solution of 6-acetamido-4-hydroxyl-[1,5]naphthyridine-3-carbonitrile (1.0 g, 4.386 mmol) was heated at reflux in POCl3 (20 ml) under nitrogen for 5 hrs. After cooling, the solvent was removed by rotary evaporation. Ice water was added to the black residue, which was cooled (ice bath) and stirred for 1 hr. The mixture was warmed to room temperature and stirred at room temperature for 1 hr. The mixture was cooled with ice bath, and made basic with NH4OH. The aqueous layer was extracted with CH2Cl2. The combined extracts were washed with water, dried (Na2SO4) and concentrated to give the title compound as a dark blue solid (200 mg, 19%).

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