Phosphorus oxychloride → 1-Chloro-4-(4-methoxyphenyl)phthalazine

HRID 1990781Notes

Reaction equation

HRID 1990781 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[C:17](=O)[NH:16][N:15]=2)=[CH:10][CH:9]=1>O>[Cl:3][C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:14]([C:11]2[CH:12]=[CH:13][C:8]([O:7][CH3:6])=[CH:9][CH:10]=2)=[N:15][N:16]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 6891034-(4-Methoxyphenyl)-1-(2H)-phthalazinone

Product 1

HCID 27723901-Chloro-4-(4-methoxyphenyl)phthalazineYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

With cooling with ice, 25 ml of phosphorus oxychloride was added to 95.05 g (20 mmol) of the obtained 4-(4-methoxyphenyl)-2H-phthalazin-1-on, 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 4.00 g (yield: 74%) of 1-chloro-4-(4-methoxyphenyl)-phthalazine 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-0e13dff9a00a4448aee64b25cee35169
Source dataset
uspto-grants-2010_01
Patent number
US07645756B2

Reaction notes

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