Hydrazine → HCID 58914783, compound

HRID 1366808Notes

Reaction equation

HRID 1366808 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:10]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:11][N:12]([CH2:14][CH2:15][CH2:16][N:17]2C(=O)C3C=CC=CC=3C2=O)[CH:13]=1.NN.C(Cl)Cl.C(#N)C>C(O)C>[NH2:17][CH2:16][CH2:15][CH2:14][N:12]1[CH:13]=[C:9]([C:3]2[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=2[Cl:1])[C:10]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:11]1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 21877088Acetonitrile methylene chlorideHCID 58914781HCID 58914781, compound

Product 1

HCID 58914783HCID 58914783, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The Pthalimido Pyrrole 4 (1 eq) was dissolved in ethanol and hydrazine (3 eq) at room temperature under nitrogen. Upon heating to reflux, the reaction generated a white precipitate. Stir at reflux until complete (˜2 h) by TLC (CH2Cl2/acetonitrile (95:5 v/v), the UV active product was at Rf=0.2) and LCMS. Upon reaching completion, the reaction was allowed to cool to room temperature and the precipitate was vacuum-filtered off using a medium to fine cintered-glass filter. The filtrate was concentrated under reduced pressure to a gummy solid. The crude material was taken up in ethanol/EtOAc (1:1 v/v), stirred and the precipitate was filtered off in the same fashion as before. The filtrate was concentrated under reduced pressure and than dried in vacuo for 10-15 min. This process of adding ethanol/EtOAc, filtering and concentrating was done one more time or as needed to remove the majority of the white precipitate and residual hydrazine. The product was then dried in vacuo overnight. The material was used without further purification. Once dried, the reaction yielded the product as a glass (˜87% yield over 2 steps).

Workup

  1. customat room temperature
  2. temperatureUpon heating
  3. temperatureto reflux
  4. filtrationthe precipitate was vacuum-filtered off
  5. filtrationfilter
  6. concentrationThe filtrate was concentrated under reduced pressure to a gummy solid
  7. stirringstirred
  8. filtrationthe precipitate was filtered off in the same fashion as before
  9. concentrationThe filtrate was concentrated under reduced pressure
  10. customthan dried in vacuo for 10-15 min
  11. filtrationThis process of adding ethanol/EtOAc, filtering
  12. concentrationconcentrating
  13. customto remove the majority of the white precipitate and residual hydrazine
  14. customThe product was then dried in vacuo overnight
  15. customThe material was used without further purification
  16. customOnce dried

Sources & evidence

ORD record
ord-dc6154038877416db16087524d822ed5
Source dataset
uspto-grants-2011_02
Patent number
US07893096B2

Reaction notes

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