Water → 1-Chloro-7-methoxy-4-(4-methoxyphenyl)phthalazine

HRID 29926Notes

Reaction equation

HRID 29926 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][C:17]([O:20][CH3:21])=[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:27])=O>>[Cl:27][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][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)=[N:8][N:9]=1

Participants

5

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 576917557-methoxy-4-(4-methoxyphenyl)-2H-phthalazin-1-one

Product 1

HCID 576917601-Chloro-7-methoxy-4-(4-methoxyphenyl)phthalazineYield 96%

Conditions

Temperature
80 °C

Procedure

19 g (67 mmol) of 7-methoxy-4-(4-methoxyphenyl)-2H-phthalazin-1-one are dissolved in 100 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 500 mL of water at 40-50° C. with stirring. The mixture is then stirred at 5° C., basified by addition of 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, 19.3 g of a beige-coloured powder are obtained (yield=96%).

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, 19.3 g of a beige-coloured powder
  7. customare obtained (yield=96%)

Sources & evidence

ORD record
ord-013126d83d8e48438d193bbafbc789d8
Source dataset
uspto-grants-2008_09
Patent number
US07423030B2

Reaction notes

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