Acetonitrile → HCID 86613927, compound

HRID 1811428Notes

Reaction equation

HRID 1811428 reaction equation
Br[CH2:2][CH2:3][CH2:4][N:5]1[C:14]2[C:9](=[C:10]([CH:15]3[O:19]CCO3)[CH:11]=[CH:12][CH:13]=2)[CH2:8][CH2:7][C:6]1=[O:20].[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([SH:28])=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+].C(#N)C>C(OCC)(=O)C.O>[Cl:21][C:22]1[CH:27]=[CH:26][C:25]([S:28][CH2:2][CH2:3][CH2:4][N:5]2[C:14]3[CH:13]=[CH:12][CH:11]=[C:10]([CH:15]=[O:19])[C:9]=3[CH2:8][CH2:7][C:6]2=[O:20])=[CH:24][CH:23]=1

Participants

7

Reactant 4

HCID 6342AcetonitrileHCID 7815p-ChlorothiophenolHCID 11430Potassium CarbonateHCID 665970461-(3-Bromopropyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-2(1H)-quinolinone

Product 1

HCID 86613927HCID 86613927, compoundYield 83.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

1-(3-Bromopropyl)-5-(1,3-dioxolan-2-yl)-3,4-dihydro-1H-quinolin-2-one (797 mg, 2.34 mmol), 4-chlorothiophenol (407 mg, 2.81 mmol) and potassium carbonate (421 mg, 3.05 mmol) were added to acetonitrile (16 ml), followed by heating under reflux for 5 hours. After cooling to room temperature, water was added to the reaction mixture, and extraction with ethyl acetate was performed. The extract was dried over sodium sulfate and concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→2:1). The purified product was concentrated under reduced pressure, and the residue was dissolved in acetone (16 ml). p-Toluenesulfonic acid monohydrate (53.5 mg) and water (3 ml) were added, followed by stirring at room temperature overnight. An aqueous solution of potassium carbonate was added to the reaction mixture, and extraction with dichloromethane was performed. The organic layer was washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated under reduced pressure to thereby obtain 700 mg (yield: 83%) of 1-[3-(4-chlorophenylsulfanyl)propyl]-2-oxo-1,2,3,4-tetrahydroquinoline-5-carboxaldehyde as a colorless oil.

Workup

  1. temperatureby heating
  2. temperatureunder reflux for 5 hours
  3. dry with materialThe extract was dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=3:1→2:1)
  6. concentrationThe purified product was concentrated under reduced pressure
  7. dissolutionthe residue was dissolved in acetone (16 ml)
  8. additionp-Toluenesulfonic acid monohydrate (53.5 mg) and water (3 ml) were added
  9. additionAn aqueous solution of potassium carbonate was added to the reaction mixture, and extraction with dichloromethane
  10. washThe organic layer was washed with a saturated sodium chloride solution
  11. dry with materialdried over anhydrous sodium sulfate
  12. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-14160605ced24e7c9fdb56d9012abd2b
Source dataset
uspto-grants-2013_01
Patent number
US08362252B2

Reaction notes

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