Hydrazine hydrate (1:1) → HCID 178470500, compound

HRID 915398Notes

Reaction equation

HRID 915398 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([O:6][C:7](=[O:22])[C:8](=O)[CH:9]([C:12](=O)[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1)[CH2:10][CH3:11])[CH3:5]>C(O)C>[CH2:4]([O:6][C:7]([C:8]1[C:9]([CH2:10][CH3:11])=[C:12]([C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)[NH:3][N:2]=1)=[O:22])[CH3:5]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 68415320HCID 68415320, compound

Product 1

HCID 178470500HCID 178470500, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Hydrazine monohydrate (0.13 ml, 3 mmol) was added at ambient temperature to a solution of 3-(4-chloro-benzoyl)-2-oxo-pentanoic acid ethyl ester (740 mg, 3 mmol) in ethanol (4 ml) under an argon atmosphere. The solution was stirred for 8 h at reflux temperature, the solvent was removed under reduced pressure and the residue partitioned between 1 M HCl/ice water and ethyl acetate. The aqueous layer was extracted two times with ethyl acetate, the combined extracts were washed with brine (3 times) and dried over sodium sulfate. Removal of the solvent under reduced pressure left an orange oil which was purified by column chromatography (silica gel, heptane/AcOEt) to give 355 mg (1.27 mmol, 49%) of the title compound as yellow crystals.

Workup

  1. temperatureat reflux temperature
  2. customthe solvent was removed under reduced pressure
  3. customthe residue partitioned between 1 M HCl/ice water and ethyl acetate
  4. extractionThe aqueous layer was extracted two times with ethyl acetate
  5. washthe combined extracts were washed with brine (3 times)
  6. dry with materialdried over sodium sulfate
  7. customRemoval of the solvent under reduced pressure
  8. waitleft an orange oil which
  9. customwas purified by column chromatography (silica gel, heptane/AcOEt)

Sources & evidence

ORD record
ord-c71c769606f748209a6575247b375dbb
Source dataset
uspto-grants-2007_09
Patent number
US07265149B2

Reaction notes

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