2-Methyl-1,3-cyclopentanedione → NSP 805

HRID 1195211Notes

Reaction equation

HRID 1195211 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:16][CH:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]1=O>C(O)C.C(O)(=O)C>[CH3:16][C:17]1[C:21](=[O:22])[CH2:20][CH2:19][C:18]=1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 130052-Methyl-1,3-cyclopentanedioneHCID 161928Ici 109,081

Product 1

HCID 130349NSP 805Yield 43.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of 0.51 g of 4,5-dihydro-6-(4-aminophenyl)-5-methyl-3(2H) pyridazinone and 0.28 g of 2-methyl-cyclopentane-1,3-dione in 5 ml of ethanol and 5 ml of acetic acid was refluxed over night. After cooling, the solution was evaporated in vacuo. The residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=20:1) and recrystallized from methanol to give 0.32 g of the title compound. m.p. 285°-286° C.

Workup

  1. temperaturewas refluxed over night
  2. temperatureAfter cooling
  3. customthe solution was evaporated in vacuo
  4. customThe residue was purified by silica gel column chromatography (eluting solvent: chloroform:methanol=20:1)
  5. customrecrystallized from methanol

Sources & evidence

ORD record
ord-1c3ed8d4a2e1438caba83df88625b24e
Source dataset
uspto-grants-1992_05
Patent number
US05110925

Reaction notes

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