Sodium hydride → 1-phenyl-4-(tetrahydro-2H-pyran-4-ylacetoxy)-1,8-naphthyridin-2(1H)-one

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Reaction Steps

In accordance with a process described in JP-61-246183A, 4-hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one was synthesized. To a suspension of the synthesized compound (715 mg, 3.0 mmol) in DMF (20 mL) was added sodium hydride (purity of about 60%, 120 mg, 3.0 mmol, 1.0 eq.). The mixture was stirred until no more hydrogen was generated, to obtain a solution. Then, tetrahydro-2H-pyran-4-ylacetyl chloride (1.2 eq.) was added thereto, and the mixture was stirred at a room temperature for 1 hour. To the mixture was added a saturated sodium hydrogencarbonate aqueous solution, and the resulting precipitate was separated by filtration, washed with water, and dried to give 1-phenyl-4-(tetrahydro-2H-pyran-4-ylacetoxy)-1,8-naphthyridin-2(1H)-one as a form of crystal (738 mg, yield 67%).

Provenance & Evidence