Hydrazine hydrate (1:1) → HCID 11275594, compound

HRID 581067Notes

Reaction equation

HRID 581067 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][CH2:13][N:14]3C(=O)C4C(=CC=CC=4)C3=O)[C:5]=2[O:4][CH2:3][CH2:2]1.O.NN>C(O)C>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[C:10]([O:11][CH2:12][CH2:13][NH2:14])[C:5]=2[O:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 86754176HCID 86754176, compound

Product 1

HCID 11275594HCID 11275594, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Cleavage of the phthalimide group of the compound obtained in Step B is carried out in ethanol in the presence of an aqueous 98% hydrazine hydrate solution (2 eq. per 1.5 g of product). It is preferable to add the latter after 10 minutes' refluxing. When the reaction is complete, the alcohol is removed under reduced pressure. The dry residue is taken up in dichloromethane in the cold in order to precipitate the phthalic hydrazide that has formed. The latter may then be removed by filtration and the recovered and concentrated filtrate is washed several times to obtain the pule product by thin-layer chromatography.

Workup

  1. additionto add the latter after 10 minutes'
  2. temperaturerefluxing
  3. customthe alcohol is removed under reduced pressure
  4. customto precipitate the phthalic hydrazide that
  5. customhas formed
  6. customThe latter may then be removed by filtration
  7. customthe recovered
  8. washconcentrated filtrate is washed several times
  9. customto obtain the pule product by thin-layer chromatography

Sources & evidence

ORD record
ord-90fba283e1c64d3eb596ca5f0fb07a84
Source dataset
uspto-grants-1999_07
Patent number
US05919814

Reaction notes

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