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

Participants

Reaction Steps

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)+.

Provenance & Evidence