Potassium Carbonate → HCID 66596986, compound

HRID 504006Notes

Reaction equation

HRID 504006 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([O:13][CH3:14])=[C:6]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8][CH2:7]2.C(=O)([O-])[O-].[K+].[K+].[C:21]1(B(O)O)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:14][O:13][C:5]1[CH:4]=[CH:3][C:2]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[C:11]2[C:6]=1[CH2:7][CH2:8][C:9](=[O:12])[NH:10]2

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 66827Phenylboronic AcidHCID 21243022HCID 21243022, compound

Product 1

HCID 66596986HCID 66596986, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

8-Bromo-5-methoxy-3,4-dihydro-1H-quinolin-2-one (10.0 g), tetrakis(triphenylphosphine)palladium (0.45 g) and potassium carbonate (5.4 g) were suspended in dioxane (100 ml), and phenylboronic acid (5.24 g) was added, followed by heating under reflux in an argon atmosphere for 2 hours. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the resulting mixture was subjected to extraction with ethyl acetate. The extract was washed twice with water, washed with a saturated sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was recrystallized from an ethyl acetate-n-hexane mixed solvent to thereby obtain 8.3 g (yield: 84%) of 5-methoxy-8-phenyl-3,4-dihydro-1H-quinolin-2-one as a light yellow powder.

Workup

  1. temperatureby heating
  2. temperatureunder reflux in an argon atmosphere for 2 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure, water
  4. additionwas added to the residue
  5. extractionthe resulting mixture was subjected to extraction with ethyl acetate
  6. washThe extract was washed twice with water
  7. washwashed with a saturated sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure
  11. customThe residue was recrystallized from an ethyl acetate-n-hexane mixed solvent

Sources & evidence

ORD record
ord-3e1047c668a44a4c8d71dfcd5ad16112
Source dataset
uspto-grants-2010_08
Patent number
US07777038B2

Reaction notes

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