Isatin → 1-(2-Diisopropylaminoethyl)isatin

HRID 868559Notes

Reaction equation

HRID 868559 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].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[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

5

Reactant 3

HCID 7054IsatinHCID 11430Potassium CarbonateHCID 779422-Chloroethyldiisopropylammonium chloride

Product 1

HCID 139344081-(2-Diisopropylaminoethyl)isatinYield 89.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

A suspension of 2.94 g of isatin, 4.20 g of 2-diisopropylaminoethyl chloride hydrochloride, and 3.17 g of anhydrous potassium carbonate in 50 ml of toluene was stirred for 4 hours at 90° C. After cooling, the reaction mixture was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was recrystallized from hexane to obtain 4.93 g of 1-(2-diisopropylaminoethyl)isatin. The chemical properties of this product are identical with those of the product obtained by Reference Example 1.

Workup

  1. temperatureAfter cooling
  2. washthe reaction mixture was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-fac8584d98b041be8e8e7bdef858f849
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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