Water → Nsp 804

HRID 1195208Notes

Reaction equation

HRID 1195208 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1.[CH3:15][CH:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]1=O.O>C1(C)C=CC=CC=1>[CH3:15][C:16]1[C:20](=[O:21])[CH2:19][CH2:18][C:17]=1[NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH2:9][CH2:10][C:11](=[O:14])[NH:12][N:13]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 130052-Methyl-1,3-cyclopentanedioneHCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one

Product 1

HCID 130345Nsp 804

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3.4 g of 4,5-dihydro-6-(4-aminophenyl)-3(2H)-pyridazinone and 2.0 of 2-methylcyclopentane-1,3-dione were suspended in 30 ml of toluene, to which a catalytic amount of p-toluene sulfonate-hydrate was add while the resulting suspension was heated to reflux with stirring for 8 hours, with removal of water as an azcotropic mexture. After cooled, deposited crude crystal was collected by filtrating, and purified by silica gel column chromatography (eluting solvent: chloroform:methanol=10:1), 4.7 g of the title compound was obtained. m.p. 284°-285° C.

Workup

  1. additionwas add while the resulting suspension
  2. temperaturewas heated
  3. temperatureto reflux
  4. temperatureAfter cooled
  5. customdeposited crude crystal was collected
  6. filtrationby filtrating
  7. custompurified by silica gel column chromatography (eluting solvent: chloroform:methanol=10:1)

Sources & evidence

ORD record
ord-e006f618bbd64060b6c2b9a2d589e920
Source dataset
uspto-grants-1992_05
Patent number
US05110925

Reaction notes

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