Water → 4-cyclohexylacetoxy-1-phenyl-1,8-naphthyridin-2(1H)-one

HRID 217372

Reaktionsgleichung

Reaktionsgleichung von HRID 217372
[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+].[CH:21]1([CH2:27][C:28](Cl)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.O>CN(C=O)C>[CH:21]1([CH2:27][C:28]([O:1][C:2]2[C:11]3[C:6](=[N:7][CH:8]=[CH:9][CH:10]=3)[N:5]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:4](=[O:18])[CH:3]=2)=[O:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2757989Cyclohexylacetyl chlorideHCID 546864734-Hydroxy-1-phenyl-1,8-naphthyridin-2(1H)-one

Produkt 1

HCID 689460384-cyclohexylacetoxy-1-phenyl-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 (953 mg, 4.0 mmol) in DMF (32 mL) was added sodium hydride (purity of about 60%, 176 mg, 4.4 mmol, 1.1 eq.), and the mixture was stirred at a room temperature for 35 minutes. Then, cyclohexylacetyl chloride (4.8 mmol, 1.2 eq.) was added thereto with cooling in an ice bath, and the mixture was stirred at a room temperature for 80 minutes. Thereafter, water was added to the reaction mixture, and the precipitate was separated by filtration and dried to give 4-cyclohexylacetoxy-1-phenyl-1,8-naphthyridin-2(1H)-one as a form of crystal (1.33 g, yield 91%).

Aufarbeitung

  1. customwas synthesized
  2. temperaturewith cooling in an ice bath
  3. stirringthe mixture was stirred at a room temperature for 80 minutes
  4. customthe precipitate was separated by filtration
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-381374e46da143758f32b92472c91773
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08193356B2

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