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

HRID 2425341Notes

Reaction equation

HRID 2425341 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.[CH2:29]([N:31](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:29]#[N:31])=[N:12][C:13]=3[CH:14]=[C:5]2[CH:4]=[CH:3]1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 70297m-Chloroperbenzoic acidHCID 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 sodium thiosulfate aqueous solution and the resulting organic phase was washed with sodium hydrogencarbonate aqueous solution and then with sodium chloride aqueous solution, and dried over anhydrous magnesium sulfate. After distilling off the solvent, acetonitrile (19.3 mL), trimethylsilylnitrile (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, sodium hydrogencarbonate aqueous 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 sodium thiosulfate aqueous solution
  3. washthe resulting organic phase was washed with sodium hydrogencarbonate aqueous solution
  4. dry with materialwith sodium chloride aqueous 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-88f05ae5077142ab9b299b2e08df96fc
Source dataset
uspto-grants-2011_06
Patent number
US07964623B2

Reaction notes

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