Hydrazine hydrate (1:1) → 5-Hydroxy-3-phenylpentanoic acid hydrazide

HRID 546732Notes

Reaction equation

HRID 546732 reaction equation
O.[NH2:2][NH2:3].[C:4]1([CH:10]2[CH2:15][CH2:14][O:13][C:12](=[O:16])[CH2:11]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[OH:13][CH2:14][CH2:15][CH:10]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH2:11][C:12]([NH:2][NH2:3])=[O:16]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 109319594-Phenyl-tetrahydropyran-2-one

Product 1

HCID 668396805-Hydroxy-3-phenylpentanoic acid hydrazide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (1.6 mL) was added to a solution of 4-phenyl-tetrahydropyran-2-one (573 mg; CAS No. 61949-75-5) in ethanol (3 mL) at room temperature, and the reaction solution was heated under reflux for three hours. The reaction solution was left to cool to room temperature and then concentrated under reduced pressure. A saturated sodium bicarbonate solution was added to the resulting residue, followed by extraction with chloroform. The resulting extract was dried over magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (elution solvent: ethyl acetate-methanol system) to obtain 492 mg of the title compound. The property value of the compound is as follows.

Workup

  1. temperaturethe reaction solution was heated
  2. temperatureunder reflux for three hours
  3. waitThe reaction solution was left
  4. concentrationconcentrated under reduced pressure
  5. additionA saturated sodium bicarbonate solution was added to the resulting residue
  6. extractionfollowed by extraction with chloroform
  7. extractionThe resulting extract
  8. dry with materialwas dried over magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (elution solvent: ethyl acetate-methanol system)

Sources & evidence

ORD record
ord-ed383d409dd143419d04af69a2c9d67f
Source dataset
uspto-grants-2011_05
Patent number
US07935815B2

Reaction notes

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