Sodium hydride → 4-hydroxy-1-phenyl-3-(4-trifluoromethoxyphenylacetyl)-1,8-naphthyridin-2(1H)-one

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 (893 mg, 3.7 mmol) in DMF (16 mL) was added sodium hydride (purity of about 60%, 360 mg, 9.0 mmol, 2.4 eq.), and the mixture was stirred until no more hydrogen was generated. Then, 4-trifluoromethoxyphenylacetyl chloride (1.2 eq.) was added thereto, and the mixture was stirred at a room temperature for 3 hours. To the mixture was added water and further added a saturated sodium hydrogencarbonate solution, and the resulting mixture was subjected to extraction with dichloromethane. The extract was dried over anhydrous magnesium sulfate, and the solvent was distilled off from the extract. The resulting residue was purified by a flash column chromatography to give 4-hydroxy-1-phenyl-3-(4-trifluoromethoxyphenylacetyl)-1,8-naphthyridin-2(1H)-one (383 mg, yield 23%).

1. customwas synthesized
2. extractionthe resulting mixture was subjected to extraction with dichloromethane
3. dry with materialThe extract was dried over anhydrous magnesium sulfate
4. distillationthe solvent was distilled off from the extract
5. customThe resulting residue was purified by a flash column chromatography

ORD 기록

ord-232611ede40e4b2daeab917ef1811aab

출처 데이터셋

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08193356B2