Isopropylamine → HCID 21287238, compound

HRID 868570Notes

Reaction equation

HRID 868570 reaction equation
Br[CH2:2][CH2:3][N:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=[O:8])[C:5]1=[O:6].[CH:15]([NH2:18])([CH3:17])[CH3:16]>CN(C)C=O>[CH:15]([NH:18][CH2:2][CH2:3][N:4]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:7](=[O:8])[C:5]1=[O:6])([CH3:17])[CH3:16]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 35427341-(2-bromoethyl)-1H-indole-2,3-dione

Product 1

HCID 21287238HCID 21287238, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4.00 g of 1-(2-bromoethyl)isatin and 13.5 ml of isopropylamine in 160 ml of dry N,N-dimethylformamide was stirred for 1 hour at 80° C. The solution was concentrated under reduced pressure and the residue was dissolved in 50 ml of a 2N-hydrochloric acid. The solution was washed with ethyl acetate, neutralized by adding an aqueous sodium bicarbonate solution, and extracted with chloroform. The chloroform layer was washed with water, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified with silica gel column chromatography (eluent: chloroform/methanol=10/1) to obtain 3.11 g of 1-(2-isopropylaminoethyl)isatin in an oil.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in 50 ml of a 2N-hydrochloric acid
  3. washThe solution was washed with ethyl acetate
  4. additionby adding an aqueous sodium bicarbonate solution
  5. extractionextracted with chloroform
  6. washThe chloroform layer was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified with silica gel column chromatography (eluent: chloroform/methanol=10/1)

Sources & evidence

ORD record
ord-14d0d713f2664e72ac607c1a65fda7ca
Source dataset
uspto-grants-1988_10
Patent number
US04780477

Reaction notes

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