Water → 1-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oxime

HRID 915004Notes

Reaction equation

HRID 915004 reaction equation
[N:1]([O-:3])=O.[Na+].O.[CH:6]([N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([CH2:16][C:17](=[O:24])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[N:10]1)([CH3:8])[CH3:7]>CC(O)=O.CCOC(C)=O>[CH:6]([N:9]1[C:14](=[O:15])[CH:13]=[CH:12][C:11]([C:16](=[N:1][OH:3])[C:17]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[O:24])=[N:10]1)([CH3:8])[CH3:7]

Participants

6

Reactant 3

HCID 962WaterHCID 23668193Sodium NitriteHCID 693314642-isopropyl-6-(2-oxo-2-phenylethyl)-3(2H)-pyridazinone

Product 1

HCID 1363499311-(1-Isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oximeYield 59.8%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

A solution of sodium nitrite (1.725 g) of water (5.42 ml) was added in portions to a solution of 2-isopropyl-6-(2-oxo-2-phenylethyl)-3(2H)-pyridazinone (2.57 g) in a mixture of AcOH (2 ml) and EtOAc (8 ml) at 20-25° C. and the mixture was stirred at the same temperature for 8 hours. EtOAc was added to the mixture, washed with sat. aq. NaHCO3 solution and brine, dried over MgSO4 and concentrated under reduced pressure to give a solid. The solid was triturated with IPE and collected by filtration to give 1-(1-isopropyl-6-oxo-1,6-dihydro-3-pyridazinyl)-2-phenyl-1,2-ethanedione 1-oxime as a solid (1.71 g), which was identical to the authentic sample (the product of Preparation 1) by melting point and IR, MS and NMR spectra.

Workup

  1. washwashed with sat. aq. NaHCO3 solution and brine
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated under reduced pressure
  4. customto give a solid
  5. customThe solid was triturated with IPE
  6. filtrationcollected by filtration

Sources & evidence

ORD record
ord-85b47aeb5b984caebb68a1bf9f5aa59b
Source dataset
uspto-grants-2007_09
Patent number
US07265120B2

Reaction notes

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