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

HRID 1993461노트

반응식

HRID 1993461 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6212Chloroform용매2회HCID 6342Acetonitrile용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-4a662aadc7fc4b5ea82981c63e0db27e
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652008B2

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