Sodium hydride → HCID 19067989, compound

HRID 1957535Notes

Reaction equation

HRID 1957535 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])[CH:9]=[CH:8]2)[CH:2]=[CH2:3].[H-].[Na+].[CH2:18](Br)[CH:19]=[C:20]([CH3:22])[CH3:21]>CN(C)C=O>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][CH:14]=1)[N:11]=[C:10]([O:15][CH2:18][CH:19]=[C:20]([CH3:22])[CH3:21])[CH:9]=[CH:8]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 700922-Butene, 1-bromo-3-methyl-HCID 19067879HCID 19067879, compound

Product 1

HCID 19067989HCID 19067989, compoundYield 34.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

10.2 Grams of 6-allyloxy-2(1H)-quinolinone was dissolved in 100 ml of dimethylformamide, then 2.2 g of 60% oily sodium hydride and 9.1 g of prenyl bromide were added thereto by the procedures similar to those employed in Reference example 7 and reacted. Then, thus obtained reaction mixture was treated and oily mixture was obtained. This mixture was subjected to separation and refining by means of a silica gel flush column chromatography in which a mixture of ethyl acetate:n-hexane (1:10 to 1:2) was used as an eluent. Colorless to light yellow oily product, which was obtained by concentrating the second eluate portion under reduced pressure, was allowed to stand at room temperature, then it was crystallized. There was obtained 4.7 g (34.9%) of 6-allyloxy-2-prenyloxy-quinoline by recrystallization from n-hexane. Colorless needle-like crystals (recrystallized from n-hexane)

Workup

  1. customreacted
  2. customThen, thus obtained reaction mixture
  3. additionwas treated
  4. customoily mixture was obtained
  5. customThis mixture was subjected to separation and refining by means of a silica gel
  6. customflush column chromatography in which
  7. additiona mixture of ethyl acetate:n-hexane (1:10 to 1:2)
  8. customColorless to light yellow oily product, which was obtained
  9. concentrationby concentrating the second eluate portion under reduced pressure
  10. customto stand at room temperature
  11. customit was crystallized

Sources & evidence

ORD record
ord-1ab4d0e2912942de8051dbc32b46add5
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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