Water → HCID 23287789, compound

HRID 367026Notes

Reaction equation

HRID 367026 reaction equation
[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]=[CH2:18])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:19])[NH:10]2)(=[O:3])[CH3:2].[H-].[Na+].[H][H].O.[CH3:25]N(C=O)C>>[C:1]([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH:17]=[CH2:18])=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:19])[N:10]2[CH3:25])(=[O:3])[CH3:2]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 23287791HCID 23287791, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23287789HCID 23287789, compound

Procedure

9 Grams of 5-acetoxy-8-allyloxy-3,4-dihydro-2(1H)-quinolinone was dissolved in 100 ml of DMF, 1.51 g of 60%-sodium hydride was added gradually in limited amounts to this solution, this reaction mixture was stirred at room temperature until generation of hydrogen gas ceased. Under stirring and ice-cooling conditions, 100 ml of water was added to this reaction mixture, extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, the dried extract was concentrated under reduced pressure. The oily product thus obtained was purified by a silica gel column chromatography, there was obtained 7 g of 5-acetoxy-8-allyloxy-3,4-dihydro-1-methyl-2(1H)-quinolinone as pale yellow oily product.

Workup

  1. additionwas added to this reaction mixture
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. extractionthe dried extract
  6. concentrationwas concentrated under reduced pressure
  7. customThe oily product thus obtained
  8. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-1bc8cc96fca64bfcba8a03c363e37831
Source dataset
uspto-grants-2000_10
Patent number
US06133264

Reaction notes

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