Potassium Hydroxide → HCID 20338091, compound

HRID 1395757Notes

Reaction equation

HRID 1395757 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[C:13]([CH:17]([CH3:21])[C:18](N)=[O:19])=[CH:14][CH:15]=[CH:16][C:3]1=2.[OH-:22].[K+].[OH-].[Na+]>C(O)C.O>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[O:5][C:4]2[C:13]([CH:17]([CH3:21])[C:18]([OH:22])=[O:19])=[CH:14][CH:15]=[CH:16][C:3]1=2

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 14798Sodium HydroxideHCID 20338070HCID 20338070, compound

Product 1

HCID 20338091HCID 20338091, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To 100 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]oxepin-4-yl)-propionamide in 2 ml of ethanol was added 400 mg of potassium hydroxide in 2 ml of water and the mixture was refluxed with stirring for 6.5 hours. After the completion of the reaction, the solvent was distilled off to obtain the residue, to which was added 2N-sodium hydroxide solution, and the resulting mixture was extracted with ethyl acetate. The aqueous layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain brown oil, which was chromatographed over silica gel, eluted with chloroform and crystallized from acetone-n-hexane to give 85 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]oxepin-4-yl)-propionic acid as pale yellow crystals having a melting point of 159°-160° C.

Workup

  1. temperaturethe mixture was refluxed
  2. customAfter the completion of the reaction
  3. distillationthe solvent was distilled off
  4. customto obtain the residue
  5. extractionthe resulting mixture was extracted with ethyl acetate
  6. extractionextracted with ethyl acetate
  7. washThe extract was washed with saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off
  10. customto obtain brown oil, which
  11. customwas chromatographed over silica gel
  12. washeluted with chloroform
  13. customcrystallized from acetone-n-hexane

Sources & evidence

ORD record
ord-7cc51d59105a482f9dcc2385a905d15e
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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