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Pyridine → HCID 86613921, Verbindung

HRID 1811412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1811412
N1C=CC=CC=1.[F:7][C:8]([F:21])([F:20])[S:9]([O:12]S(C(F)(F)F)(=O)=O)(=[O:11])=[O:10].O[C:23]1[CH:32]=[CH:31][C:30]([CH3:33])=[C:29]2[C:24]=1[CH2:25][CH2:26][C:27](=[O:34])[NH:28]2>ClCCl>[CH3:33][C:30]1[CH:31]=[CH:32][C:23]([O:12][S:9]([C:8]([F:21])([F:20])[F:7])(=[O:11])=[O:10])=[C:24]2[C:29]=1[NH:28][C:27](=[O:34])[CH2:26][CH2:25]2
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 1049PyridineHCID 67749Trifluoromethanesulfonic anhydrideHCID 10976036HCID 10976036, Verbindung

Produkt 1

HCID 86613921HCID 86613921, VerbindungAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Pyridine (6.2 ml) and trifluoromethanesulfonic anhydride (10.3 ml) were added with stirring at 0° C. to an anhydrous dichloromethane solution (30 ml) of 5-hydroxy-8-methyl-3,4-dihydro-1H-quinolin-2-one (9.0 g), followed by stirring for 1 hour. The resulting mixture was concentrated under reduced pressure, water was added to the residue, and extraction with dichloromethane was performed. The extract was washed with water, an aqueous potassium hydrogensulfate solution and water in this order, and dried over anhydrous sodium sulfate. After concentration under reduced pressure, the residue was recrystallized from an ethyl acetate-diisopropyl ether mixed solvent to thereby obtain 28 g (yield: 97%) of 8-methyl-5-trifluoromethanesulfonyloxy-3,4-dihydro-1H-quinolin-2-one as a light brown powder.

Aufarbeitung

  1. concentrationThe resulting mixture was concentrated under reduced pressure, water
  2. additionwas added to the residue, and extraction with dichloromethane
  3. washThe extract was washed with water
  4. dry with materialan aqueous potassium hydrogensulfate solution and water in this order, and dried over anhydrous sodium sulfate
  5. concentrationAfter concentration under reduced pressure
  6. customthe residue was recrystallized from an ethyl acetate-diisopropyl ether mixed solvent

Quellen und Nachweise

ORD-Eintrag
ord-b11f46d20bf2463cab79e8bad279791d
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08362252B2

Notizen zur Reaktion

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