Sodium Hydroxide → trans-Octahydroquinolin-2-one

HRID 1779999Notes

Reaction equation

HRID 1779999 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 12265804trans-Octahydroquinolin-2-oneYield 74.1%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6dac46498e35486896fda7816fc82cf4
Source dataset
uspto-grants-1997_05
Patent number
US05629322

Reaction notes

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