Sodium Hydroxide → trans-Octahydroquinolin-2-one

HRID 1779999Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1779999
[NH:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][C:5]=2[CH2:4][CH2:3][C:2]1=[O:11].C([O-])=O.[Na+].[OH-].[Na+]>C(O)=O>[NH:1]1[C@H:10]2[C@@H:5]([CH2:6][CH2:7][CH2:8][CH2:9]2)[CH2:4][CH2:3][C:2]1=[O:11]

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 7360043,4,5,6,7,8-Hexahydro-2(1H)-quinolinoneHCID 2723810Sodium Formate

Produkt 1

HCID 12265804trans-Octahydroquinolin-2-oneAusbeute 74,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A mixture of 1 g (6.62 mmol) of 3,4,5,6,7,8,-hexahydro-2(1H)-quinolinone, 2.8 g (41 mmol) of sodium formate and 5 mL of formic acid was heated to reflux for 1 day The reaction mixture was then cooled and 20% sodium hydroxide solution was added to make it basic. This mixture was then extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate and the solvent was removed to give a crude product. This was purified on silica gel using ethyl acetate as solvent to provide 752 mg of the desired product with about 10% of the cis-isomer. Recrystallization of this material from cyclohexane did not improve the ratio of the isomers.

Aufarbeitung

  1. temperaturewas heated
  2. temperatureto reflux for 1 day The reaction mixture
  3. temperaturewas then cooled
  4. extractionThis mixture was then extracted with ethyl acetate
  5. dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
  6. customthe solvent was removed
  7. customto give a crude product
  8. customThis was purified on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-6dac46498e35486896fda7816fc82cf4
Quelldatensatz
uspto-grants-1997_05
Patentnummer
US05629322

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