Sodium hydride → 6-allyloxy-3,4-dihydro-1-prenyl-2-(1H)-quinolinone

HRID 1957534Notes

Reaction equation

HRID 1957534 reaction equation
[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[NH:11][C:10](=[O:15])[CH2:9][CH2:8]2)[CH:2]=[CH2:3].[H-].[Na+].[H][H].[CH2:20](Br)[CH:21]=[C:22]([CH3:24])[CH3:23]>CN(C)C=O.O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH2:20][CH:21]=[C:22]([CH3:24])[CH3:23])[C:10](=[O:15])[CH2:9][CH2:8]2)[CH:2]=[CH2:3]

Participants

7

Reactant 4

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 190680326-(allyloxy)-3,4-dihydroquinolin-2(1H)-oneHCID 178418361HCID 178418361, compound

Product 1

HCID 190679146-allyloxy-3,4-dihydro-1-prenyl-2-(1H)-quinolinoneYield 59.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

10.2 Grams of 6-allyloxy-3,4-dihydro-2(1H)-quinolinone was dissolved in 100 ml of dimethyl-formamide (DMF), then at room temperature, 2.2 g of 60% oily sodium hydride was added little by little thereto, and the reaction mixture was stirred at 25° to 40° C. until generation of hydrogen was stopped. The reaction mixture was cooled to room temperature, 9.1 g of prenyl bromide was added thereto and stirred at room temperature for 8 hours. After the reaction was completed, water was added, and the reaction mixture was extracted with methylene chloride. The methylene chloride extract was washed with water and an aqueous solution saturated with sodium chloride in this order, then thus washed extract was dried with anhydrous magnesium sulfate. Magnesium sulfate was removed by filtration and concentrated. Thus obtained oily residue was subjected to refining and separating by means of a silica gel flush column chromatography by using mixed solvent of ethyl acetate:n-hexane (1:10 to 1:2) as an eluent to obtain 10.2 g (59.7%) of 6-allyloxy-3,4-dihydro-1-prenyl-2-(1H)-quinolinone.

Workup

  1. extractionthe reaction mixture was extracted with methylene chloride
  2. extractionThe methylene chloride extract
  3. washwas washed with water
  4. washan aqueous solution saturated with sodium chloride in this order, then thus washed
  5. extractionextract
  6. dry with materialwas dried with anhydrous magnesium sulfate
  7. customMagnesium sulfate was removed by filtration
  8. concentrationconcentrated
  9. customseparating by means of a silica gel
  10. customflush column chromatography
  11. additionby using mixed solvent of ethyl acetate:n-hexane (1:10 to 1:2) as an eluent

Sources & evidence

ORD record
ord-c2641e0d106e4d17a438014d26a11dec
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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