Hydrochloric Acid → HCID 19067942, compound

HRID 1957552Notes

Reaction equation

HRID 1957552 reaction equation
[CH2:1]([C:4]1[C:13]([OH:14])=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:18])[NH:9]2)[CH:2]=[CH2:3].Cl.[C:20](=[O:23])(O)[O-].[Na+]>O1C=CCCC1>[CH2:1]([C:4]1[C:13]([O:14][CH:3]2[CH2:2][CH2:1][CH2:4][CH2:20][O:23]2)=[C:12]([CH2:15][CH:16]=[CH2:17])[CH:11]=[C:10]2[C:5]=1[CH2:6][CH2:7][C:8](=[O:18])[NH:9]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 19067992HCID 19067992, compound

Product 1

HCID 19067942HCID 19067942, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 80803,4-dihydro-2H-pyranSolvent

Conditions

Temperature
60 °C

Procedure

5,7-Diallyl-3,4-dihydro-6-hydroxy-2(1H)-quinolinone (24.3 g) obtained in Example 26 was dissolved in 100 ml of 3,4-dihydro-2H-pyran, then 1 ml of concentrated hydrochloric acid was added thereto and stirred at 60° C. for 8 hours. The reaction mixture was cooled, and neutralized with 10% sodium bicarbonate solution, then extracted with ethyl acetate. The extract was washed with an aqueous solution saturated with sodium bicarbonate, and concentrated under reduced pressure. Recrystallized from ethyl acetate-n-hexane, there was obtained 14 g (58%) of 5,7-diallyl-3,4-dihydro-6-(2-tetrahydropyranyloxy)-2(1H)-quinolinone.

Workup

  1. temperatureThe reaction mixture was cooled
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution saturated with sodium bicarbonate
  4. concentrationconcentrated under reduced pressure
  5. customRecrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-b720bc8c456945a08fb13769e98f07a3
Source dataset
uspto-grants-1998_07
Patent number
US05786367

Reaction notes

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