Acetic Acid → HCID 67067321, compound

HRID 599591Notes

Reaction equation

HRID 599591 reaction equation
C(O)(=O)C.[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]2[CH2:16][CH2:15][O:14][C:13]2=[O:17])=[CH:8][CH:7]=1.[NH2:18][NH2:19].N>CO.C(OCC)(=O)C>[F:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH2:16][CH2:15][OH:14])[C:13]([NH:18][NH2:19])=[O:17])=[CH:8][CH:7]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 9321HydrazineHCID 22013226HCID 22013226, compound

Product 1

HCID 67067321HCID 67067321, compoundYield 31.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Acetic acid (1 mL) was added to a solution of 3-(4-fluorophenyl)dihydrofuran-2-one (393 mg) and hydrazine (699 mg) in methanol (10 mL), and the reaction solution was heated to reflux for two hours. The reaction solution was left to cool to room temperature. Then, ethyl acetate and concentrated aqueous ammonia were added to the reaction solution, and the organic layer was separated. The resulting organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. Chloroform was added to the residue, and the precipitated solid was collected by filtration to obtain 147 mg of the title compound. The property values of the compound are as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureto reflux for two hours
  3. waitThe reaction solution was left
  4. customthe organic layer was separated
  5. dry with materialThe resulting organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. additionChloroform was added to the residue
  8. filtrationthe precipitated solid was collected by filtration

Sources & evidence

ORD record
ord-b107cb6310c3429e805db945ccc07133
Source dataset
uspto-grants-2011_03
Patent number
US07897632B2

Reaction notes

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