Hydrazine hydrate (1:1) → HCID 9877790, compound

HRID 270169Notes

Reaction equation

HRID 270169 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6](=[O:25])[C:7]3[C:8](=[CH:11][S:12][C:13]=3[N:14]3C(=O)C4C(=CC=CC=4)C3=O)[C:9]=2[CH:10]=1.CC1C2C(=O)C3C(=CSC=3N3C(=O)C4C(=CC=CC=4)C3=O)C=2C=CC=1.O.NN>C(O)C>[NH2:14][C:13]1[S:12][CH:11]=[C:8]2[C:9]3[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=3[C:6](=[O:25])[C:7]=12

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 21964329HCID 21964329, compoundHCID 21964340HCID 21964340, compound

Product 1

HCID 9877790HCID 9877790, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-(5-methyl-8-oxo-8H-2-thia-cyclopenta[a]inden-1-yl)-isoindole-1,3-dione and 2-(7-methyl-8-oxo-8H-2-thia-cyclopenta[a]inden-1-yl)-isoindole-1,3-dione (0.45 mmol, Example & 3, Part E) in absolute ethanol (5 mL) was added hydrazine hydrate (0.5 mmol). The suspension was heated to reflux for one hour, cooled to room temperature, concentrated in vacuo, and the residue dissolved in methylene chloride. The solution was chilled to 5° C. for one hour, during which time the phthaloyl hydrazide precipitated. The precipitate was removed by filtration, the filtrate concentrated in vacuo, and the residue purified by column chromatography on silica gel, eluting with a 4:1 mixture of petroleum ether:ethyl acetate. Fractions containing the individual products were pooled, evaporated, and each product was isolated after recrystallization from petroleum ether.

Workup

  1. temperatureThe suspension was heated
  2. temperatureto reflux for one hour
  3. concentrationconcentrated in vacuo
  4. dissolutionthe residue dissolved in methylene chloride
  5. temperatureThe solution was chilled to 5° C. for one hour, during which time the phthaloyl hydrazide
  6. customprecipitated
  7. customThe precipitate was removed by filtration
  8. concentrationthe filtrate concentrated in vacuo
  9. customthe residue purified by column chromatography on silica gel
  10. washeluting with a 4:1 mixture of petroleum ether
  11. additionFractions containing the individual products
  12. customevaporated
  13. customeach product was isolated
  14. customafter recrystallization from petroleum ether

Sources & evidence

ORD record
ord-40e8d02c85614839ade2b64a1f6ec703
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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