1,3-Cyclopentanedione → HCID 14882925, compound

HRID 1195210Notes

Reaction equation

HRID 1195210 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.[C:16]1(=O)[CH2:20][CH2:19][C:18](=[O:21])[CH2:17]1>C(O)C.C(O)(=O)C>[O:21]=[C:18]1[CH2:19][CH2:20][C:16]([NH:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[CH:9]([CH3:15])[CH2:10][C:11](=[O:14])[NH:12][N:13]=3)=[CH:4][CH:3]=2)=[CH:17]1

Participants

5

Reactant 2

HCID 774661,3-CyclopentanedioneHCID 161928Ici 109,081

Product 1

HCID 14882925HCID 14882925, compoundYield 33.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

0.51 g of 4,5-dihydro-6-(4-aminophenyl)-5-methyl-3(2H)-pyridazinone and 0.25 g of cyclopentane-1,3-dione were suspended in a mixture of 5 ml of ethanol and 5 ml of acetic acid and the resulting suspension was refluxed for 7 hours. After cooled, deposited crude crystal was collected by filtrating and recrystallized from DMF-heptane-CHCl3 to give 0.24 g of the title compound. m.p. >300° C. NMR (solvent DMSO-d6 -CDCl3) δ 1.20 (d, 3H), 2.32-3.32 (m, 7H), 5.60 (S, 1H), 7.56 (dd, 4H), 9.82 (S, 1H), 10.80 (S, 1H).

Workup

  1. temperaturethe resulting suspension was refluxed for 7 hours
  2. temperatureAfter cooled
  3. customdeposited crude crystal was collected
  4. filtrationby filtrating
  5. customrecrystallized from DMF-heptane-CHCl3

Sources & evidence

ORD record
ord-fad0018b48a84501acccd0874bc245c3
Source dataset
uspto-grants-1992_05
Patent number
US05110925

Reaction notes

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