Ethyl Acetate → HCID 66604605, compound

HRID 334450Notes

Reaction equation

HRID 334450 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][C:9]=2[C:13]([O:15]CC)=O)=[CH:4][CH:3]=1.C(OCC)(=O)C.O.[NH2:25][NH2:26]>O1CCOCC1.C(O)C>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:12]=[CH:11][O:10][C:9]=2[C:13]([NH:25][NH2:26])=[O:15])=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 24654Hydrazine hydrate (1:1)HCID 66598908HCID 66598908, compound

Product 1

HCID 66604605HCID 66604605, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Procedure

After ethyl 3-(4-aminophenyl)-2-furan carboxylate (7 g) was dissolved in a mixed solvent of 1,4-dioxane (7 mL) and ethanol (3 mL), hydrazine monohydrate (11.4 mL) was added. The mixture was heated at reflux for 6 hours. Ethyl acetate (100 mL) was added to the reaction mixture, and the mixture was washed with a saturated sodium chloride solution. Thereafter, the organic layer was dried over magnesium sulfate and concentrated under reduced pressure, thereby giving 3.8 g of the target compound as a solid.

Workup

  1. additionwas added
  2. temperatureThe mixture was heated
  3. temperatureat reflux for 6 hours
  4. washthe mixture was washed with a saturated sodium chloride solution
  5. dry with materialThereafter, the organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-68469b5fd6ba48e0a64fdc4971bf94cb
Source dataset
uspto-grants-2014_11
Patent number
US08883824B2

Reaction notes

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