Hydrochloric Acid → HCID 54356706, compound

HRID 367027Notes

Reaction equation

HRID 367027 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]=[CH2:15])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:16])[NH:7]2.Cl.[C:18](=[O:21])([O-])[O-].[K+].[K+].C(OCC)(=O)C.[CH3:30][CH2:31][CH2:32][CH2:33]CC>O1C=CCCC1>[O:21]1[CH2:18][CH2:33][CH2:32][CH2:31][CH:30]1[O:1][C:2]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][CH:14]=[CH2:15])=[C:8]2[C:3]=1[CH2:4][CH2:5][C:6](=[O:16])[NH:7]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 12751739HCID 12751739, compoundHCID 21226206Ethyl acetate hexane

Product 1

HCID 54356706HCID 54356706, compound

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Procedure

6 Grams of 5-hydroxy-3,4-dihydro-8-allyloxy-2(1H)-quinolinone was dissolved in 20 ml of dihydropyran, to this solution was added 2 ml of concentrated hydrochloric acid, then refluxed by heating for 1 hour. To this reaction mixture was added 5 g of potassium carbonate powder and stirred, then concentrated under reduced pressure. The residue thus obtained was extracted with ethyl acetate, the extract was washed with water, dried over anhydrous magnesium sulfate, again concentrated under reduced pressure to obtained pale yellow oily product. A mixed solvent of ethyl acetate-n-hexane was added to the oily product and allowed to stand for crystallization. There was obtained 8 g of 5-tetrahydropyranyloxy-8-allyloxy-3,4-dihydro-2(1H)-quinolinone as white amorphous product.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 1 hour
  3. concentrationconcentrated under reduced pressure
  4. customThe residue thus obtained
  5. extractionwas extracted with ethyl acetate
  6. washthe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationagain concentrated under reduced pressure
  9. customto obtained pale yellow oily product
  10. customto stand for crystallization

Sources & evidence

ORD record
ord-c20e5e6644794350a165cde4382be833
Source dataset
uspto-grants-2000_10
Patent number
US06133264

Reaction notes

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