Benzene → 4-phenyl-2,5,6,7-tetrahydro-1H-cyclopenta[d]pyridazin-1-one

HRID 469673Notes

Reaction equation

HRID 469673 reaction equation
[C:1]1(=O)[C:5]2[CH2:6][CH2:7][CH2:8][C:4]=2[C:3](=[O:9])O1.[Cl-].[Cl-].[Cl-].[Al+3].O.O.[NH2:17][NH2:18].[CH:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(=S)=S.CCO>[C:19]1([C:1]2[C:5]3[CH2:6][CH2:7][CH2:8][C:4]=3[C:3](=[O:9])[NH:17][N:18]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

8

Reactant 5

HCID 241BenzeneHCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 3248541H,3H,4H,5H,6H-cyclopenta(c)furan-1,3-dioneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 669665454-phenyl-2,5,6,7-tetrahydro-1H-cyclopenta[d]pyridazin-1-one

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6348Carbon DisulfideSolvent

Procedure

5,6-dihydro-1H-cyclopenta[c]furan-1,3(4H)-dione (1 g, 7 mmol) was added slowly to a well-stirred suspension of aluminum trichloride (1.9 g, 14 mmol) in 15 mL of benzene and 15 mL of CS2. The red reaction mixture was refluxed for 1.5 hours. After cooling, the mixture was poured into water, and extracted with CHCl3. The organic layer was dried (Na2SO4), filtered and concentrated to afford a solid. The solid was dissolved in 20 mL of EtOH, and 5 mL of hydrazine hydrate was added. The mixture was refluxed for 12 hours, allowed to cool, and filtered. The solid collected was washed with water, and dried to afford the title compound. MS (APCI+) M/Z 213 (M+H)+.

Workup

  1. customThe red reaction mixture
  2. temperaturewas refluxed for 1.5 hours
  3. temperatureAfter cooling
  4. extractionextracted with CHCl3
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto afford a solid
  9. temperatureThe mixture was refluxed for 12 hours
  10. temperatureto cool
  11. filtrationfiltered
  12. customThe solid collected
  13. washwas washed with water
  14. customdried

Sources & evidence

ORD record
ord-5dcf3407557344e59c194e575ffd71dd
Source dataset
uspto-grants-2014_01
Patent number
US08629143B2

Reaction notes

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