Hydrazine hydrate (1:1) → HCID 178470478, compound

HRID 1914729Notes

Reaction equation

HRID 1914729 reaction equation
C([O:3][C:4]1[C:5](=O)[CH:6]([C:10](=O)[C:11]([O:13][CH2:14][CH3:15])=[O:12])[CH2:7][CH2:8][CH:9]=1)C.O.[NH2:19][NH2:20]>C(O)C>[O:3]=[C:4]1[C:5]2[NH:20][N:19]=[C:10]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH2:7][CH2:8][CH2:9]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 44235432Ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate

Product 1

HCID 178470478HCID 178470478, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

10.0 g (42 mmol) of ethyl (3-ethoxy-2-oxocyclohex-3-en-1-yl)(oxo)acetate were dissolved in 100 mL of ethanol, 2.1 mL of hydrazine hydrate were added and the solution stirred at reflux for one day. The solvent was then evaporated and the residue redissolved with dichloromethane. The organic layer was washed with water, dried over Na2SO4 and concentrated. The crude was triturated with diethyl ether and filtered to give 6.0 g of the title compound (70% yield).

Workup

  1. temperatureat reflux for one day
  2. customThe solvent was then evaporated
  3. dissolutionthe residue redissolved with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customThe crude was triturated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-3da0bf00771942eb89d6632dc99a229a
Source dataset
uspto-grants-2013_12
Patent number
US08614220B2

Reaction notes

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