Potassium Hydroxide → 6-(Pyridin-3-yl)-3,4-dihydroquinolin-2(1H)-one

HRID 1649746Notes

Reaction equation

HRID 1649746 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]2.[N:13]1[CH:18]=[CH:17][CH:16]=[C:15](B(CC)CC)[CH:14]=1.[OH-].[K+]>O1CCCC1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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>[N:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:2]2[CH:3]=[C:4]3[C:9](=[CH:10][CH:11]=2)[NH:8][C:7](=[O:12])[CH2:6][CH2:5]3)[CH:14]=1

Participants

7

Reactant 3

HCID 14797Potassium HydroxideHCID 6428513-(Diethylboryl)pyridineHCID 143732816-Bromo-3,4-dihydroquinolin-2(1H)-one

Product 1

HCID 137288626-(Pyridin-3-yl)-3,4-dihydroquinolin-2(1H)-one

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.0 g of 6-bromo-3,4-dihydrocarbostyril, 520 mg of 3-pyridyldiethylborane and 205 mg. of tetrakis(triphenylphosphine)palladium in 20 ml of tetrahydrofuran was added 600 mg of powdered potassium hydroxide and 114 mg of tetrabutylammonium bromide. The mixture was refluxed for 48 hours under an inert atmosphere and the solvent then removed under reduced pressure. The residue was extracted with a mixture of 10% of methanol in methylene chloride and the organic solution washed with water and dried over anhydrous sodium sulfate. The solvent was removed from the dried solution under reduced pressure, and the residue chromatographed on silica gel, eluting with 5% methanol in methylene chloride to give 6-(3-pyridyl)-3,4-dihydrocarbostyril, m.p. 180°-182° C.

Workup

  1. temperatureThe mixture was refluxed for 48 hours under an inert atmosphere
  2. customthe solvent then removed under reduced pressure
  3. extractionThe residue was extracted with a mixture of 10% of methanol in methylene chloride
  4. washthe organic solution washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was removed from the dried solution under reduced pressure
  7. customthe residue chromatographed on silica gel
  8. washeluting with 5% methanol in methylene chloride

Sources & evidence

ORD record
ord-9c4a9a4b4da0453bbc1b1dd4f660e3ae
Source dataset
uspto-grants-1990_05
Patent number
US04921862

Reaction notes

Loading…