Hydrazine hydrate (1:1) → HCID 53671996, compound

HRID 1107790Notes

Reaction equation

HRID 1107790 reaction equation
O.[NH2:2][NH2:3].[CH2:4]([N:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[C:10]([CH:15]=O)=[C:9]1[C:17](Cl)=[CH:18][CH2:19][C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH:5]=[CH:6][CH3:7]>C(O)C>[CH2:4]([N:8]1[C:9]2=[C:17]([CH2:18][CH2:19][C:20]3[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=3)[N:2]=[N:3][CH:15]=[C:10]2[C:11]([CH3:14])=[C:12]1[CH3:13])[CH:5]=[CH:6][CH3:7]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 54105048HCID 54105048, compound

Product 1

HCID 53671996HCID 53671996, compoundYield 62.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

0.10 g (0.0020 mole) of hydrazine hydrate was added to a solution of 0.39 g (0.00113 mole) of 1-(2-butenyl)-2-[1-chloro-3-(4-fluorophenyl)-1-propenyl]-3-formyl-4,5-dimethylpyrrole in 7 ml of ethanol and the resulting mixture was stirred at 75° C. for an hour. After completion of the reaction, the reaction mixture was concentrated under reduced pressure and the concentrate was diluted with ice-water. The aqueous mixture was extracted twice with 30 ml of ethyl acetate. The combined extracts were washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the residue was purified by column chromatography through silica gel using a 50:1 mixture of chloroform and methanol as an eluent to give 0.23 g of the title compound (cis/trans=22/78) as white powdery crystals.

Workup

  1. customAfter completion of the reaction
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. additionthe concentrate was diluted with ice-water
  4. extractionThe aqueous mixture was extracted twice with 30 ml of ethyl acetate
  5. washThe combined extracts were washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customthe residue was purified by column chromatography through silica gel using
  9. additiona 50:1 mixture of chloroform and methanol as an eluent

Sources & evidence

ORD record
ord-bc6d905b25ff4d2180304ceef7fe08de
Source dataset
uspto-grants-2000_05
Patent number
US06063782

Reaction notes

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