Water → 6-Bromo-2-[2-(diisopropylamino)ethyl]phthalazin-1(2H)-one

HRID 622124Notes

Reaction equation

HRID 622124 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][N:6]=[CH:5]2.[OH-].[K+].Cl.[CH:16]([N:19]([CH:23]([CH3:25])[CH3:24])[CH2:20][CH2:21]Cl)([CH3:18])[CH3:17].O>CS(C)=O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:21][CH2:20][N:19]([CH:23]([CH3:25])[CH3:24])[CH:16]([CH3:18])[CH3:17])[N:6]=[CH:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 779422-Chloroethyldiisopropylammonium chlorideHCID 115359186-Bromophthalazin-1(2h)-one

Product 1

HCID 212933346-Bromo-2-[2-(diisopropylamino)ethyl]phthalazin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

6-Bromophthalazinone (11.2 gm, 0.05 mole) was slurried in 80 ml dimethylsulfoxide. To this was added 22 ml 45% KOH (0.25 mole). After stirring 10 minutes 16 gm 2-(diisopropylamino)ethyl chloride hydrochloride was added and the mixture stirred for 18 hours. A water bath was used to moderate the slightly exothermic reaction (temperature <=25°). Water (100 ml) was added to the reaction mixture, which was then stirred another hour.

Workup

  1. additionwas added
  2. customA water bath was used
  3. customthe slightly exothermic reaction (temperature <=25°)
  4. stirringwas then stirred another hour

Sources & evidence

ORD record
ord-8beea11fd514416690c0bd6c6de67784
Source dataset
uspto-grants-1988_09
Patent number
US04769369

Reaction notes

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