Hydrazine hydrate (1:1) → HCID 69309728, compound

HRID 2053951Notes

Reaction equation

HRID 2053951 reaction equation
[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]([CH:6]1[CH2:10][CH2:9][CH2:8][C:7]1=O)=O.O.[NH2:15][NH2:16]>C(O)C>[CH3:1][O:2][CH:3]([O:12][CH3:13])[C:4]1[C:6]2[CH2:10][CH2:9][CH2:8][C:7]=2[NH:16][N:15]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 62744851HCID 62744851, compound

Product 1

HCID 69309728HCID 69309728, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

5.7 g (30.6 mmol) of 2-(2,2-dimethoxyacetyl)cyclopentanone is dissolved in 50 mL of ethanol and after the addition of 6 g (96 mmol) of hydrazine hydrate (80%) refluxed for 2.5 hours. The ethanol is distilled off, the residue is combined with water and extracted with ethyl acetate. The organic extracts are dried and concentrated by evaporation. The crude product is chromatographed on silica gel, eluting with petroleum ether/ethyl acetate 1:2. Yield: 3.1 g (56%).

Workup

  1. temperaturerefluxed for 2.5 hours
  2. distillationThe ethanol is distilled off
  3. extractionextracted with ethyl acetate
  4. customThe organic extracts are dried
  5. concentrationconcentrated by evaporation
  6. customThe crude product is chromatographed on silica gel
  7. washeluting with petroleum ether/ethyl acetate 1:2

Sources & evidence

ORD record
ord-97dd058ad30840888c5fd07a2997bc8d
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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