Acetic Acid → 3-acetyl-7,8-dihydrocyclopenta[e]indazol-6(3H)-one

HRID 2076353Notes

Reaction equation

[CH3:1][C:2]1[C:10]([NH:11][C:12](=[O:14])[CH3:13])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:15].C([O-])(=O)C.[K+].C(O)(=O)C.C(OC(=O)C)(=O)C.O1CCOCCOCCOCCOCCOCC1.[N:50](OCCC(C)C)=O>C(Cl)(Cl)Cl>[C:12]([N:11]1[C:10]2[CH:9]=[CH:8][C:7]3[C:6](=[O:15])[CH2:5][CH2:4][C:3]=3[C:2]=2[CH:1]=[N:50]1)(=[O:14])[CH3:13]

Participants

Conditions

Temperature: 65 °C

Procedure

A stirred mixture of N-(4-methyl-1-oxo-2,3-dihydro-1H-inden-5-yl)acetamide (20.00 g, 98.40 mmol), potassium acetate (19.32 g, 197 mmol), acetic acid (11.3 mL, 197 mmol), acetic anhydride (18.6 mL, 197 mmol) and 1,4,7,10,13,16-hexaoxacyclooctadecane (5.20 g, 19.7 mmol) in 600 mL of chloroform was heated at 65° C. and isopentyl nitrite (33.0 mL, 246 mmol) was added during 10 minutes. The mixture was stirred at 65° C. for 23 hours and was then allowed to cool to room temperature. The reaction mixture was diluted with chloroform and washed successively with saturated NaHCO3 (2×), water and brine. After drying over Na2SO4, the solution was concentrated to low volume under vacuum and flash chromatographed on silica gel eluting with EtOAc/dichloroethane (0:100 to 10:90) to give 3-acetyl-7,8-dihydrocyclopenta[e]indazol-6(3H)-one as a yellow solid.

Workup

temperatureto cool to room temperature
washwashed successively with saturated NaHCO3 (2×), water and brine
dry with materialAfter drying over Na2SO4
concentrationthe solution was concentrated to low volume under vacuum and flash
customchromatographed on silica gel eluting with EtOAc/dichloroethane (0:100 to 10:90)

Sources & evidence

ORD record: ord-e481772143234f78a702a55266499dfe
Source dataset: uspto-grants-2011_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07923568B2

Reaction notes

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