Sodium hydride → 1-phenyl-4-(2-phenylbutyryloxy)-1,8-naphthyridin-2(1H)-one

HRID 217379

Reaktionsgleichung

Reaktionsgleichung von HRID 217379
[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].[C:23]1([CH:29]([CH2:33][CH3:34])[C:30](Cl)=[O:31])[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.C(=O)([O-])O.[Na+]>CN(C=O)C>[C:12]1([N:5]2[C:6]3[C:11](=[CH:10][CH:9]=[CH:8][N:7]=3)[C:2]([O:1][C:30](=[O:31])[CH:29]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:33][CH3:34])=[CH:3][C:4]2=[O:18])[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Komponenten

7

Edukt 5

HCID 24758Sodium hydrideHCID 981732-Phenylbutyryl chlorideHCID 516892Sodium BicarbonateHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 689486761-phenyl-4-(2-phenylbutyryloxy)-1,8-naphthyridin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 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 (1.19 g, 5.0 mmol) in DMF (40 mL) was added sodium hydride (purity of about 60%, 200 mg, 5.0 mmol, 1.0 eq.). The mixture was stirred until no more hydrogen was generated, to obtain a solution. Then, 2-phenylbutyryl chloride (0.92 mL, 5.5 mmol, 1.1 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-(2-phenylbutyryloxy)-1,8-naphthyridin-2(1H)-one as a form of crystal (1.63 g, yield 85%).

Aufarbeitung

  1. customwas synthesized
  2. customto obtain a solution
  3. customthe resulting precipitate was separated by filtration
  4. washwashed with water
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-4eabe78405764933b2382d7e4272cf0a
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193356B2

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