Isatin → 1-(2-Diisopropylaminoethyl)isatin

HRID 868558Notes

Reaction equation

HRID 868558 reaction equation
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].Cl.[CH:13]([N:16]([CH:20]([CH3:22])[CH3:21])[CH2:17][CH2:18]Cl)([CH3:15])[CH3:14].[H-].[Na+]>C1(C)C=CC=CC=1.CN(C)C=O>[CH:13]([N:16]([CH:20]([CH3:22])[CH3:21])[CH2:17][CH2:18][N:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3])([CH3:15])[CH3:14]

Participants

6

Reactant 3

HCID 7054IsatinHCID 24758Sodium hydrideHCID 779422-Chloroethyldiisopropylammonium chloride

Product 1

HCID 139344081-(2-Diisopropylaminoethyl)isatin

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

2.94 Grams of isatin and 4.00 g of 2-diisopropylaminoethyl chloride hydrochloride were suspended in a mixture of 50 ml of dry toluene and 10 ml of dry N,N-dimethylformamide, and 1.60 g of sodium hydride (60% dispersion in mineral oil) was added to the suspension with stirring under ice-cooling. The mixture was stirred for 30 minutes at room temperature, and then heated at 80° C. for 19 hours. The reaction mixture was concentrated under reduced pressure, and water was added to the residue. The mixture was extracted with benzene, and the benzene layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane to obtain 4.62 g of 1-(2-diisopropylaminoethyl)isatin having a melting point of 60°-61° C.

Workup

  1. additionwas added to the suspension
  2. temperaturecooling
  3. stirringThe mixture was stirred for 30 minutes at room temperature
  4. concentrationThe reaction mixture was concentrated under reduced pressure, and water
  5. additionwas added to the residue
  6. extractionThe mixture was extracted with benzene
  7. washthe benzene layer was washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-954fc61c3697484ca449d08d69fedd17
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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