Sodium methanolate methanol → 7-Fluoro-1,5-naphthyridin-2(1H)-one

HRID 385491Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 385491
[NH2:1][C:2]1[C:3](/[CH:9]=[CH:10]/[C:11]([O:13]CC)=O)=[N:4][CH:5]=[C:6]([F:8])[CH:7]=1.C[O-].[Na+].CO>CO>[F:8][C:6]1[CH:7]=[C:2]2[C:3]([CH:9]=[CH:10][C:11](=[O:13])[NH:1]2)=[N:4][CH:5]=1

Komponenten

4

Edukt 2

HCID 23694274Sodium methanolate methanol2×HCID 68105283ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate

Produkt 1

HCID 469008017-Fluoro-1,5-naphthyridin-2(1H)-oneAusbeute 60,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 0.36 g of ethyl (2E)-3-(3-amino-5-fluoropyridin-2-yl)acrylate in 3 mL of methanol, 0.37 g of a 28% sodium methoxide/methanol solution was added at room temperature, and the mixture was heated under reflux while stirring for 2 hours 40 minutes. Thereto was added 72 mg of a 28% sodium methoxide/methanol solution, and the mixture was heated under reflux while stirring for 1 hour. The reaction mixture was cooled to room temperature, the solvent was then distilled off under reduced pressure, and the resultant residue was charged with ethyl acetate and water and adjusted to pH 6.7 with 1 mol/L hydrochloric acid. The solvent was distilled off under reduced pressure, the solid was filtered off and washed with water and diethyl ether to obtain 0.17 g of 7-fluoro-1,5-naphthyridin-2(1H)-one as a light brown solid.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux
  3. temperaturethe mixture was heated
  4. temperatureunder reflux
  5. stirringwhile stirring for 1 hour
  6. distillationthe solvent was then distilled off under reduced pressure
  7. additionthe resultant residue was charged with ethyl acetate and water
  8. distillationThe solvent was distilled off under reduced pressure
  9. filtrationthe solid was filtered off
  10. washwashed with water and diethyl ether

Quellen und Nachweise

ORD-Eintrag
ord-6ea08abf008e40a596b9fe0ca9eb13b1
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08367831B2

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