Hydrochloric Acid → HCID 20338054, compound

HRID 1395758Notes

Reaction equation

HRID 1395758 reaction equation
O=[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.[OH2:22].NN.[OH-].[Na+].Cl>C(O)C.O.C(O)COCCO>[CH:16]1[C:3]2[CH2:2][CH2:8][C:7]3[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=3[O:5][C:4]=2[C:13]([CH:17]([CH3:21])[C:18]([OH:22])=[O:19])=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 20338070HCID 20338070, compound

Product 1

HCID 20338054HCID 20338054, compound

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Procedure

To 80 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]oxepin-4-yl)-propionamide in 4 ml of ethanol was added 0.3 ml of hydrazine hydrate and the mixture was refluxed with stirring for 8 hours. The solvent was distilled off to obtain pale yellow oil, to which were added 3 ml of diethylene glycol and 400 mg of sodium hydroxide, and the resulting mixture was stirred at 125° C. for 1 hour. To the mixture was added water and the resulting solution was acidified with hydrochloric acid and extracted with ethyl acetate. The organic layer was extracted with saturated sodium hydrogencarbonate solution. 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 pale yellow crystals, which were recrystallized from benzene-n-hexane, and there was obtained 37 mg of 2-(10,11-dihydro dibenzo[b,f]oxepin-4-yl)-propionic acid as pale yellow crystals having a melting point of 133°-133.5° C.

Workup

  1. temperaturethe mixture was refluxed
  2. distillationThe solvent was distilled off
  3. customto obtain pale yellow oil
  4. stirringthe resulting mixture was stirred at 125° C. for 1 hour
  5. extractionextracted with ethyl acetate
  6. extractionThe organic layer was extracted with saturated sodium hydrogencarbonate solution
  7. extractionextracted with ethyl acetate
  8. washThe extract was washed with saturated sodium chloride solution
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off
  11. customto obtain pale yellow crystals, which
  12. customwere recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-2e606f41dd884a888584b6cc13679cd7
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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