Water → 7-bromo-2,2-dimethyl-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-one

HRID 1929430Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1929430
[H-].[Na+].[NH2:3][C:4]1[C:9]([OH:10])=[CH:8][C:7]([Br:11])=[CH:6][N:5]=1.Br[C:13]([CH3:20])([CH3:19])[C:14](OCC)=[O:15].O>CN(C)C=O>[Br:11][C:7]1[CH:6]=[N:5][C:4]2[NH:3][C:14](=[O:15])[C:13]([CH3:20])([CH3:19])[O:10][C:9]=2[CH:8]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 11745Propanoic acid, 2-bromo-2-methyl-, ethyl esterHCID 24758Sodium hydrideHCID 116940412-Amino-5-bromo-3-hydroxypyridine

Produkt 1

HCID 577420407-bromo-2,2-dimethyl-2H,3H,4H-pyrido(3,2-b)(1,4)oxazin-3-oneAusbeute 20,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a suspension of sodium hydride (60% dispersion in mineral oil, 0.68 g) in N,N-dimethylformamide (15 mL) was added dropwise a solution of 2-amino-5-bromopyridin-3-ol (3.22 g) in N,N-dimethylformamide (25 mL) at room temperature over a period of 10 minutes, and the mixture was stirred at room temperature for 20 minutes. To the mixture was added dropwise ethyl α-bromoisobutyrate (3.32 g) over a period of 20 minutes, and the reaction mixture was stirred at room temperature for 1 hour and at 80° C. for 2 hours. After cooling, to the reaction mixture was added cold water, and the mixture was extracted with ethyl acetate. The organic layer was washed successively water and brine, dried over magnesium sulfate and concentrated in vacuo by a half volume. The precipitates were collected by filtration to give 7-bromo-2,2-dimethyl-2H-pyrido[3,2-b][1,4]oxazin-3(4H)-one (0.90 g) was obtained as a powder.

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 1 hour and at 80° C. for 2 hours
  2. temperatureAfter cooling, to the reaction mixture
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed successively water and brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated in vacuo by a half volume
  7. filtrationThe precipitates were collected by filtration

Quellen und Nachweise

ORD-Eintrag
ord-852a5360b28f46a29adcce880a2b6ee9
Quelldatensatz
uspto-grants-2012_05
Patentnummer
US08188073B2

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