6-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-one → HCID 178467132, compound

HRID 1195209Notes

Reaction equation

HRID 1195209 reaction equation
[C:1]([C:4]1[C:5](=O)[CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8][C:9]=1[O:10]C)(=[O:3])[CH3:2].[NH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:23][CH2:24][C:25](=[O:28])[NH:26][N:27]=2)=[CH:18][CH:17]=1>C(O)C>[C:1]([C:4]1[C:9](=[O:10])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=1[NH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]2[CH2:23][CH2:24][C:25](=[O:28])[NH:26][N:27]=2)=[CH:18][CH:17]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 6767506-(4-Aminophenyl)-4,5-dihydropyridazin-3(2H)-oneHCID 12768999HCID 12768999, compound

Product 1

HCID 178467132HCID 178467132, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

230 mg of 2-acetyl-5,5-dimethyl-3-methoxy-2-cyclohexene-1-one and 284 mg of 4,5-dihydro-6-(4-aminophenyl)-3(2H)-pyridazinone was suspended in 2 ml of ethanol, and the resulting mixture was heated to reflux for an hour. After cooled, crude crystal was collected by filtrating, and purified by silica gel column chromatography (eluting solvent: chloroform:methanol=30:1). 390 mg of the title compound was obtained. m.p. 212.0°-213.5° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for an hour
  3. temperatureAfter cooled
  4. customcrude crystal was collected
  5. filtrationby filtrating
  6. custompurified by silica gel column chromatography (eluting solvent: chloroform:methanol=30:1)

Sources & evidence

ORD record
ord-e61109311dde4bc6ac2e57a016424087
Source dataset
uspto-grants-1992_05
Patent number
US05110925

Reaction notes

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