Phosphorus oxychloride → 3-chloro-6-(4-methoxyphenyl)pyridazine

HRID 1990774Notes

Reaction equation

HRID 1990774 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:19]=[N:18][C:17](O)=[CH:16][CH:15]=2)=[CH:10][CH:9]=1>O>[Cl:3][C:17]1[N:18]=[N:19][C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 28101666-(4-Methoxyphenyl)-2,3-dihydropyridazin-3-one

Product 1

HCID 122575013-chloro-6-(4-methoxyphenyl)pyridazineYield 40%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling with ice, 50 ml of phosphorus oxychloride was added to 10.00 g (49.5 mmol) of the obtained 6-(4-methoxyphenyl)-pyridazin-3-ol, and the reaction liquid was stirred under reflux for 6 hours. Water was added to the reaction liquid, extracted with chloroform, and the organic layer was washed with saturated saline water. This was dried with anhydrous sodium sulfate, and concentrated under reduced pressure to obtain 4.41 g (yield: 40%) of 3-chloro-6-(4-methoxyphenyl)-pyridazine as a white solid.

Workup

  1. customthe reaction liquid
  2. temperatureunder reflux for 6 hours
  3. extractionextracted with chloroform
  4. washthe organic layer was washed with saturated saline water
  5. dry with materialThis was dried with anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-936e47842d8540a98e4314fa99ceaf21
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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