Hydrochloric Acid → 4-methoxyacetoxy-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 217368

Reaktionsgleichung

Reaktionsgleichung von HRID 217368
[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].[CH3:23][O:24][CH2:25][C:26](Cl)=[O:27].Cl>CN(C=O)C.O>[CH3:23][O:24][CH2:25][C:26]([O: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])[CH:3]=1)=[O:27]

Komponenten

8

Edukt 5

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 96623Methoxyacetyl chlorideHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-oneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 689480664-methoxyacetoxy-1-phenyl-1,8-naphthyridin-2(1H)-oneAusbeute 73 %

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 (20 mL) was added sodium hydride (purity of about 60%, 192 mg, 4.8 mmol, 1.3 eq.), and the mixture was stirred until no more hydrogen was generated. Then, methoxyacetyl chloride (1.07 g, 9.9 mmol, 2.6 eq.) was added thereto, and the mixture was stirred at a room temperature for 50 minutes. To the mixture was added water. The resulting mixture was acidified with concentrated hydrochloric acid, and then the resulting precipitate was separated by filtration and dried to give 4-methoxyacetoxy-1-phenyl-1,8-naphthyridin-2(1H)-one (847 mg, yield 73%).

Aufarbeitung

  1. customwas synthesized
  2. customthe resulting precipitate was separated by filtration
  3. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8cb787f441ec49de8defc03ca7d03e3b
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193356B2

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