Ethanol → HCID 13134789, compound

HRID 355115Notes

Reaction equation

HRID 355115 reaction equation
O=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[N:12][C:6]=2[O:5][C:4]2[CH:13]=[CH:14][C:15]([CH2:17][C:18](N)=[O:19])=[CH:16][C:3]1=2.O.NN.C([OH:26])C.[OH-].[Na+]>O.C(O)COCCO>[N:12]1[C:6]2[O:5][C:4]3[CH:13]=[CH:14][C:15]([CH2:17][C:18]([OH:19])=[O:26])=[CH:16][C:3]=3[CH2:2][CH2:8][C:7]=2[CH:9]=[CH:10][CH:11]=1

Participants

7

Reactant 4

HCID 702Ethanol2×HCID 14798Sodium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 13134787HCID 13134787, compound

Product 1

HCID 13134789HCID 13134789, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8117Diethylene GlycolSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 20 mg of (5,6-dihydro-6-oxo benzo[b]pyrido-[3,2-f]oxepin-8-yl)-acetamide, 0.5 ml of hydrazine hydrate and 1.5 ml of ethanol was refluxed for 1 hour. The solvent and excess hydrazine hydrate were removed by distillation to obtain a residue, to which was added ethanol. Thereafter, the solvent was distilled off to obtain a yellow oil, to which were added 0.1 g of sodium hydroxide and 3 ml of dry diethylene glycol. The mixture was stirred at 100° C. for 20 minutes and then at 120° C. for 2.5 hours. After cooling, to this was added water, and the mixture was washed with ethyl acetate. The aqueous layer was acidified with acetic acid and extracted with ethyl acetate. The extract was washed with water and a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a solid, which was chromatographed over 1 g of silica gel and eluted with chloroform, thereby yielding 3.5 mg (yield: 18%) of (5,6-dihydrobenzo[b]pyrido[3,2-f]oxepin-8-yl)-acetic acid as white needle crystals having a melting point of 203°-204° C.

Workup

  1. temperaturewas refluxed for 1 hour
  2. customThe solvent and excess hydrazine hydrate were removed by distillation
  3. customto obtain a residue
  4. distillationThereafter, the solvent was distilled off
  5. customto obtain a yellow oil
  6. waitat 120° C. for 2.5 hours
  7. temperatureAfter cooling
  8. washthe mixture was washed with ethyl acetate
  9. extractionextracted with ethyl acetate
  10. washThe extract was washed with water
  11. dry with materiala saturated sodium chloride solution and dried over anhydrous sodium sulfate
  12. distillationThe solvent was distilled off
  13. customto obtain a solid, which
  14. customwas chromatographed over 1 g of silica gel
  15. washeluted with chloroform

Sources & evidence

ORD record
ord-4a87090bbcc848c4bf59d2c3b0ff97b5
Source dataset
uspto-grants-1983_03
Patent number
US04377702

Reaction notes

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