Triethylamine → 2,2,9-Trimethyl-2H-pyrano[2,3-g]quinoline-7-carbonitrile

HRID 1993461Notes

Reaction equation

HRID 1993461 reaction equation
[CH3:1][C:2]1([CH3:17])[O:16][C:6]2=[CH:7][C:8]3[C:9]([CH3:15])=[CH:10][CH:11]=[N:12][C:13]=3[CH:14]=[C:5]2[CH:4]=[CH:3]1.ClC1C=CC=C(C(OO)=O)C=1.C[Si]([C:33]#[N:34])(C)C.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(Cl)(Cl)Cl.C(#N)C.CO>[CH3:1][C:2]1([CH3:17])[O:16][C:6]2=[CH:7][C:8]3[C:9]([CH3:15])=[CH:10][C:11]([C:33]#[N:34])=[N:12][C:13]=3[CH:14]=[C:5]2[CH:4]=[CH:3]1

Participants

9

Reactant 5

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 82115Trimethylsilyl cyanideHCID 516892Sodium BicarbonateHCID 591344012,2,9-Trimethyl-2H-pyrano[2,3-g]quinoline

Product 1

HCID 672473152,2,9-Trimethyl-2H-pyrano[2,3-g]quinoline-7-carbonitrileYield 55%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×HCID 6342AcetonitrileSolvent

Procedure

To a solution of 2,2,9-trimethyl-2H-pyrano[2,3-g]quinoline (4.36 g, 19.3 mmol) in chloroform (43.6 mL), a solution of m-chloroperbenzoic acid (7.35 g, 42.6 mmol) in chloroform (17.4 mL)-methanol (4.36 mL) was added dropwise at room temperature and the resulting mixture was stirred at room temperature for 1 hour. Upon the completion of the reaction, the reaction solution was extracted with aqueous sodium thiosulfate solution and the resulting organic phase was washed with aqueous sodium hydrogencarbonate solution and then with aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, acetonitrile (19.3 mL), trimethylsilylcyanide (7.27 mL, 57.9 mmol) and triethylamine (5.38 mL, 38.6 mmol) were added to the residue at room temperature, and the resulting solution was stirred at 70° C. for 3.5 hours. Upon the completion of the reaction, aqueous sodium hydrogencarbonate solution was added to the reaction solution, and it was extracted with chloroform and dried over anhydrous magnesium sulfate. After distilling off the solvent, the residue was purified by column chromatography (hexane/ethyl acetate=2/1) and the aimed product was obtained (yield: 55%).

Workup

  1. customUpon the completion of the reaction
  2. extractionthe reaction solution was extracted with aqueous sodium thiosulfate solution
  3. washthe resulting organic phase was washed with aqueous sodium hydrogencarbonate solution
  4. dry with materialwith aqueous sodium chloride solution, and dried over anhydrous magnesium sulfate
  5. additionwere added to the residue at room temperature
  6. stirringthe resulting solution was stirred at 70° C. for 3.5 hours
  7. additionwas added to the reaction solution, and it
  8. extractionwas extracted with chloroform
  9. dry with materialdried over anhydrous magnesium sulfate
  10. distillationAfter distilling off the solvent
  11. customthe residue was purified by column chromatography (hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-4a662aadc7fc4b5ea82981c63e0db27e
Source dataset
uspto-grants-2010_01
Patent number
US07652008B2

Reaction notes

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