Water → 4-Chloro-6-methoxy-1-phenylphthalazine

HRID 29920Notes

Reaction equation

HRID 29920 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[N:8][NH:9][C:10]2=O)=[CH:5][CH:4]=1.O.[OH-].[Na+].P(Cl)(Cl)([Cl:25])=O>>[Cl:25][C:10]1[C:11]2[C:6](=[CH:5][CH:4]=[C:3]([O:2][CH3:1])[CH:12]=2)[C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:8][N:9]=1

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 692140027-Methoxy-4-phenylphthalazin-1(2H)-one

Product 1

HCID 860618334-Chloro-6-methoxy-1-phenylphthalazine

Conditions

Temperature
80 °C

Procedure

7-Methoxy-4-phenyl-2H-phthalazin-1-one (740 mg, 2.9 mmol) is dissolved in 7 mL of phosphoryl chloride. The solution is heated at 80° C. for 2 hours. The reaction medium is cooled to room temperature and then poured slowly into 200 mL of water with stirring. The mixture is then stirred at 5° C., basified with 35% sodium hydroxide solution and then extracted with dichloromethane. The organic phase is washed with water and then with brine and dried over anhydrous sodium sulfate. After filtration and evaporation under reduced pressure, 750 mg of product are obtained in the form of a beige-coloured powder.

Workup

  1. temperatureThe reaction medium is cooled to room temperature
  2. stirringThe mixture is then stirred at 5° C.
  3. extractionextracted with dichloromethane
  4. washThe organic phase is washed with water
  5. dry with materialwith brine and dried over anhydrous sodium sulfate
  6. filtrationAfter filtration and evaporation under reduced pressure, 750 mg of product
  7. customare obtained in the form of a beige-coloured powder

Sources & evidence

ORD record
ord-4ca0a4dbf1d846bbbc4c7e230604b898
Source dataset
uspto-grants-2008_09
Patent number
US07423030B2

Reaction notes

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