Potassium Carbonate → HCID 12861683, compound

HRID 367030Notes

Reaction equation

HRID 367030 reaction equation
C([O:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:22])[NH:10]2)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO>[OH:4][C:5]1[CH:14]=[CH:13][C:12]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][O:17]2)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:22])[NH:10]2

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 12751880HCID 12751880, compound

Product 1

HCID 12861683HCID 12861683, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

9.16 Grams of 5-acetoxy-8-tetrahydropyranyloxy-3,4-dihydro-2(1H)-quinolinone was dissolved in 200 ml of methanol, to this solution was added 45 ml of an aqueous solution of 10%-potassium carbonate, refluxed by heating for 1 hour, then concentrated to dryness under reduced pressure, there was obtained 5-hydroxy-8-tetrahydropyranyloxy-3,4-dihydro-2(1H)-quinolinone. This product was suspended in 100 ml of DMF, further 4.1 g of potassium carbonate was added to this suspension and stirred. To this mixture was added 3 ml of allyl bromide at room temperature and stirred for 8 hours. To this reaction mixture was added 200 ml of water, and extracted with ethyl acetate. The extract was washed with water, dried over anhydrous magnesium sulfate, concentrated under reduced pressure. The residue was recrystallized from ethyl acetate-n-hexane, there was obtained 6 g of 8-tetrahydropyranyloxy-5-allyloxy-3,4-dihydro-2(1H)-quinolinone as white solid product.

Workup

  1. temperaturerefluxed
  2. temperatureby heating for 1 hour
  3. concentrationconcentrated to dryness under reduced pressure

Sources & evidence

ORD record
ord-d92495e51f9c4cbf92e3e8dc6748481c
Source dataset
uspto-grants-2000_10
Patent number
US06133264

Reaction notes

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