Isatin → HCID 1636607, compound

HRID 1388346Notes

Reaction equation

HRID 1388346 reaction equation
[H-].[Na+].[NH:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]1=[O:13].[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18]Cl>CCOCC.CN(C)C=O>[Cl:14][CH2:15][CH2:16][CH2:17][CH2:18][N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5](=[O:12])[C:4]1=[O:13]

Participants

6

Reactant 3

HCID 7054IsatinHCID 80591,4-DichlorobutaneHCID 24758Sodium hydride

Product 1

HCID 1636607HCID 1636607, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (50% dispersion in oil, 1.63 g, 34 mmole) under dry nitrogen was washed with 50 ml of ether to remove the oil. The ether was separated by decantation. Dimethylformamide (25 ml) was added to the ether wet sodium hydride. A solution of 2,3-indolinedione (isatin, 5 g, 34 mmole) and 1,4-dichlorobutane (21.6 g, 18.6 ml, 0.17 mmole) in 200 ml of dimethylformamide was added dropwise over 1 hour, maintaining the temperature at 25°-28° C. The resulting solution was stirred for 1 hour at room temperature. The reaction mixture was filtered, and the filtrate evaporated to 30 ml and diluted with 50 ml of methylene chloride. The resulting mixture was again filtered, the filtrate evaporated to dryness and the residue slurried in 200 ml of ether. The ether was decanted from a drum and evaporated to yield the title product [830 mg, Rf 0.55 1:1 ethyl acetate:hexane)].

Workup

  1. customto remove the oil
  2. customThe ether was separated by decantation
  3. additionDimethylformamide (25 ml) was added to the ether wet sodium hydride
  4. temperaturemaintaining the temperature at 25°-28° C
  5. filtrationThe reaction mixture was filtered
  6. customthe filtrate evaporated to 30 ml
  7. additiondiluted with 50 ml of methylene chloride
  8. filtrationThe resulting mixture was again filtered
  9. customthe filtrate evaporated to dryness
  10. customThe ether was decanted from a drum
  11. customevaporated

Sources & evidence

ORD record
ord-777c3f4edebf4cce954f46d5b6875101
Source dataset
uspto-grants-1984_02
Patent number
US04431649

Reaction notes

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