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

HRID 217365

Reaktionsgleichung

Reaktionsgleichung von HRID 217365
[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:4](=[O:18])[CH:3]=1.[H-].[Na+].[H][H].[F:23][C:24]([F:37])([F:36])[O:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][C:33](Cl)=[O:34])=[CH:28][CH:27]=1.C(=O)([O-])O.[Na+]>CN(C=O)C.O>[OH:1][C:2]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:4](=[O:18])[C:3]=1[C:33](=[O:34])[CH2:32][C:29]1[CH:30]=[CH:31][C:26]([O:25][C:24]([F:36])([F:23])[F:37])=[CH:27][CH:28]=1

Komponenten

8

Edukt 5

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-oneHCID 574300964-(Trifluoromethoxy)phenylacetyl chlorideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 689454074-hydroxy-1-phenyl-3-(4-trifluoromethoxyphenylacetyl)-1,8-naphthyridin-2(1H)-oneAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-232611ede40e4b2daeab917ef1811aab
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193356B2

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