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Water → 7-trifluoromethyl-1H-pyrido[2,3-b][1,4]oxazin-2-one

HRID 1943657
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1943657
C[O:2][C:3](=O)[CH2:4][O:5][C:6]1[C:11]([N+:12]([O-])=O)=[CH:10][C:9]([C:15]([F:18])([F:17])[F:16])=[CH:8][N:7]=1.[Sn](Cl)(Cl)(Cl)Cl.O>Cl>[F:16][C:15]([F:18])([F:17])[C:9]1[CH:8]=[N:7][C:6]2[O:5][CH2:4][C:3](=[O:2])[NH:12][C:11]=2[CH:10]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 24287Tin tetrachlorideHCID 66936440(3-Nitro-5-trifluoromethyl-pyridin-2-yloxy)-acetic acid methyl ester

Produkt 1

HCID 669364877-trifluoromethyl-1H-pyrido[2,3-b][1,4]oxazin-2-oneAusbeute 62 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidLösungsmittel

Versuchsvorschrift

In a 10 ml flask, (3-nitro-5-trifluoromethyl-pyridin-2-yloxy)-acetic acid methyl ester (84 mg, 0.30 mmol) was dissolved in concentrated hydrochloric acid (1.5 ml) and then tin tetrachloride (227 mg, 1.2 mmol) was added thereto. The mixture was stirred for 30 minutes at 80□. After completion of the reaction, water was added thereto at room temperature and the mixture was extracted with a solvent of methanol: dichloromethane=1:9. The combined organic layer was dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica eluting with a solvent of methanol:dichloromethane=1:50. The fractions containing the product were collected and evaporated to obtain white solid (40 mg, 62%).

Aufarbeitung

  1. additionwas added
  2. extractionat room temperature and the mixture was extracted with a solvent of methanol
  3. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate (Na2SO4)
  4. filtrationfiltered
  5. customevaporated under reduced pressure
  6. customThe residue was purified by column chromatography on silica eluting with a solvent of methanol
  7. additionThe fractions containing the product
  8. customwere collected
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-c69f8e450071457faa9239e8ddd480b6
Quelldatensatz
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08394792B2

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