Hydrazine hydrate (1:1) → HCID 9964471, compound

HRID 270226Notes

Reaction equation

HRID 270226 reaction equation
[O:1]=[C:2]1[C:14]2[C:10](=[CH:11][S:12][C:13]=2[N:15]2C(=O)C3C(=CC=CC=3)C2=O)[CH2:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.O.NN>C(O)C>[NH2:15][C:13]1[S:12][CH:11]=[C:10]2[CH2:9][C:8]3[C:3]([C:2](=[O:1])[C:14]=12)=[CH:4][CH:5]=[CH:6][CH:7]=3

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 21964384HCID 21964384, compound

Product 1

HCID 9964471HCID 9964471, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-[4-oxo-9H-naphtho[2,3-c]thiophene-3-yl]-isoindole-1,3-dione (0.45 mmol, Example 32, Part G) in absolute ethanol (5 mL) is added hydrazine hydrate (0.5 mmol). The mixture is heated to reflux for one hour, cooled to room temperature, concentrated in vacuo, and the residue dissolved in methylene chloride. The solution is chilled to 5° C. for one hour, during which time the phthaloyl hydrazide precipitates. The precipitate is 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 product are collected, evaporated, and the product recrystallized.

Workup

  1. temperatureThe mixture is heated
  2. temperatureto reflux for one hour
  3. concentrationconcentrated in vacuo
  4. dissolutionthe residue dissolved in methylene chloride
  5. temperatureThe solution is chilled to 5° C. for one hour, during which time the phthaloyl hydrazide
  6. customprecipitates
  7. customThe precipitate is 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 product
  12. customare collected
  13. customevaporated
  14. customthe product recrystallized

Sources & evidence

ORD record
ord-f8458d9edb0a4061a0f1620d78c3561f
Source dataset
uspto-grants-2008_11
Patent number
US07449490B2

Reaction notes

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