Water → HCID 178456632, compound

HRID 915033Notes

Reaction equation

HRID 915033 reaction equation
[CH:1]([N:4]1[C:9](=[O:10])[CH:8]=[CH:7][C:6]([CH:11]([NH:20][CH2:21][C:22]([O:24]CC)=O)[C:12](=O)[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:5]1)([CH3:3])[CH3:2].C([O-])(=O)C.[NH4+:31].O.C([O-])(O)=O.[Na+]>CC(O)=O.CCOC(C)=O>[OH:24][C:22]1[N:31]=[C:12]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:11]([C:6]2[CH:7]=[CH:8][C:9](=[O:10])[N:4]([CH:1]([CH3:2])[CH3:3])[N:5]=2)=[N:20][CH:21]=1

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 517165Ammonium AcetateHCID 86600912HCID 86600912, compound

Product 1

HCID 178456632HCID 178456632, compoundYield 24.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of ethyl {[1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-oxo-2-phenylethyl]amino}acetate (14.0 g) and ammonium acetate (21.0 g) in AcOH (60 ml) was refluxed with stirring for 2 hours. Water, aq. NaHCO3 and EtOAc were added to the reaction mixture. The organic layer was separated, and dried over MgSO4. The solvent was removed in vacuo. The residue was purified by silica gel column chromatography eluted with a mixture of n-hexane and EtOAc. The fractions were concentrated in vacuo to obtain 6-(5-hydroxy-3-phenyl-2-pyrazinyl)-2-isopropyl-3(2H)-pyridazinone (3.0 g) as white powder.

Workup

  1. temperaturewas refluxed
  2. customThe organic layer was separated
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed in vacuo
  5. customThe residue was purified by silica gel column chromatography
  6. washeluted with a mixture of n-hexane and EtOAc
  7. concentrationThe fractions were concentrated in vacuo

Sources & evidence

ORD record
ord-88da19d034cf4e7e9fe4f0b695468f27
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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