Hydrochloric Acid → HCID 23287793, compound

HRID 367028Notes

Reaction equation

HRID 367028 reaction equation
O1CCCCC1[O:7][C:8]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH:20]=[CH2:21])=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:22])[NH:13]2.[H-].[Na+].[H][H].[CH2:27](Cl)[CH:28]=[C:29]([CH3:31])[CH3:30].Cl>CN(C=O)C.O>[OH:7][C:8]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][CH:20]=[CH2:21])=[C:14]2[C:9]=1[CH2:10][CH2:11][C:12](=[O:22])[N:13]2[CH2:27][CH:28]=[C:29]([CH3:31])[CH3:30]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 104291-Chloro-3-methyl-2-buteneHCID 24758Sodium hydrideHCID 54356706HCID 54356706, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 23287793HCID 23287793, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

7 Grams of 5-tetrahydropyranyloxy-8-allyloxy-3,4-dihydro-2(1H)-quinolinone was dissolved in 50 ml of DMF, then 1 g of 60%-sodium hydride was added gradually in limited amounts to this solution, the reaction mixture was stirred at room temperature until generation of hydrogen gas ceased. To this reaction mixture was added 2.7 g of prenyl chloride, stirred at room temperature for 8 hours. To this mixture was added 100 ml of water and stirred, the mixture was acidified by adding concentrated hydrochloric acid, stirred at 60° C. for 1 hour to remove the tetrahydropyranyl group at 5-position. The mixture was extracted with ethyl acetate, and washed with water, dried over anhydrous magnesium sulfate, then concentrated under reduced pressure. The oily product thus obtained was purified by a silica gel column chromatography, there was obtained 4.2 g of 5-hydroxy-8-allyloxy-3,4-dihydro-1-prenyl-2(1H)-quinolinone as pale yellow oily product.

Workup

  1. stirringstirred
  2. stirringstirred at 60° C. for 1 hour
  3. customto remove the tetrahydropyranyl group at 5-position
  4. extractionThe mixture was extracted with ethyl acetate
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe oily product thus obtained
  9. customwas purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-f5b2d8ac454c4913aa0081e1911559b4
Source dataset
uspto-grants-2000_10
Patent number
US06133264

Reaction notes

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