Diisopropyl Ether → HCID 22449318, compound

HRID 2187035Notes

Reaction equation

HRID 2187035 reaction equation
[NH:1]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]3[CH2:10][CH2:11][CH2:12][CH:3]([C:4]=23)[C:2]1=[O:13].[H-].[Na+].[C:16]([O:19][CH2:20][CH3:21])(=[O:18])[CH3:17].[CH:22](OC(C)C)(C)C>CN(C=O)C.O>[CH2:20]([O:19][C:16]([CH2:17][CH2:22][C:3]12[CH2:12][CH2:11][CH2:10][C:5]3[C:4]1=[C:9]([CH:8]=[CH:7][CH:6]=3)[NH:1][C:2]2=[O:13])=[O:18])[CH3:21]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 5993752a,3,4,5-Tetrahydrobenzo[cd]indol-2(1H)-one

Product 1

HCID 22449318HCID 22449318, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(RS)-2a,3,4,5-tetrahydro-1H-benz[cd]indol-2-one(3.46 g, 20 mmol) was dissolved in anhydrous N,N,-dimethylformamide (20 ml). Then, 60% sodium hydride (0.8 g, 20 mmol) was added thereto and the resulting mixture was stirred at room temperature for 1 hour. Successively the reaction mixture obtained was cooled to −20° C., and ethyl 3-bromo propionate (2.55 ml, 20 mmol) was added thereto. The resulting mixture was stirred at room temperature for further 1 hour. Ethyl acetate and water were added thereto to extract a reaction product. The ethyl acetate solution was washed with saturated saline solution and then dried over anhydrous sodium sulfate, and then the solvent was evaporated under reduced pressure to obtain a reaction product. Thereafter, diisopropyl ether was added to the resulting reaction product to crystallized the same. Thus, the above-described object compound was obtained in an amount of 3.80 g (yield 70%).

Workup

  1. customSuccessively the reaction mixture obtained
  2. temperaturewas cooled to −20° C.
  3. stirringThe resulting mixture was stirred at room temperature for further 1 hour
  4. extractionto extract a reaction product
  5. washThe ethyl acetate solution was washed with saturated saline solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. customto obtain a reaction product
  9. customto crystallized the same
  10. customThus, the above-described object compound was obtained in an amount of 3.80 g (yield 70%)

Sources & evidence

ORD record
ord-56a4298cafd4430ba0cdbfad81ec8c76
Source dataset
uspto-grants-2002_06
Patent number
US06407112B1

Reaction notes

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