Sodium hydride → 4-(2-phenylpropionyloxy)-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one

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In accordance with a process described in JP-61-246183A, 4-hydroxy-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one was synthesized. To a suspension of the synthesized compound (919 mg, 3.0 mmol) in DMF (24 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, 2-phenylpropionyl 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 4-(2-phenylpropionyloxy)-1-(3-trifluoromethylphenyl)-1,8-naphthyridin-2(1H)-one as a form of crystal (1.00 g, yield 76%).

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