Hydrogen Peroxide → Methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

HRID 39672

반응식

HRID 39672 반응식
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([CH:19]=[O:20])=[CH:9][C:8]1=[O:21].P([O-])(O)(O)=O.[Na+].OO.Cl([O-])=O.[Na+].[N+](=C)=[N-].[C:37](=O)([O-])[OH:38].[Na+]>C(Cl)(Cl)Cl.C(O)(=O)C.C(OCC)C.C(OCC)(=O)C.O.C(#N)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[CH2:6][N:7]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][CH3:18])[CH:15]=2)[C:10]([C:19]([O:38][CH3:37])=[O:20])=[CH:9][C:8]1=[O:21]

참가 물질

13

반응물 6

HCID 784Hydrogen PeroxideHCID 9550DiazomethaneHCID 516892Sodium BicarbonateHCID 23668197Sodium ChloriteHCID 23672064Monosodium phosphateHCID 593978441-(1,3-Dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbaldehyde

생성물 1

HCID 59398163Methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate

시약·촉매·용매 6

HCID 176Acetic Acid용매HCID 962Water용매3회HCID 3283Diethyl Ether용매HCID 6212Chloroform용매HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

실험 절차

To a mixed solution of 2 mL of acetonitrile containing 0.30 g of 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carbaldehyde and 1 mL of water, a solution of 1 mL of water containing 0.88 g of sodium dihydrogen phosphate, 0.18 mL of a 30% hydrogen peroxide solution and 0.19 g of a sodium chlorite were added, and the mixture was stirred at room temperature for 1 hour and 30 minutes. Water and ethyl acetate were added thereto. The organic layer was separated, and the aqueous layer was extracted twice with ethyl acetate. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was dissolved in chloroform, thereto was added a diethyl ether solution containing 0.09 g of diazomethane, and the resultant solution was left to stand for 10 minutes. After adding 0.5 mL of acetic acid, an aqueous saturated sodium hydrogen carbonate solution was added thereto. The organic layer was separated, and the aqueous layer was extracted with chloroform. The organic layer and the extract were combined, the resultant solution was washed with an aqueous saturated sodium chloride solution and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue thus obtained was purified by silica gel column chromatography [eluent; chloroform:methanol=100:1] to obtain 0.20 g of a pale yellow oily substance, methyl 1-(1,3-dioxolan-2-ylmethyl)-7-methoxy-2-oxo-1,2-dihydroquinoline-4-carboxylate.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer was extracted twice with ethyl acetate
  3. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue thus obtained
  7. waitto stand for 10 minutes
  8. customThe organic layer was separated
  9. extractionthe aqueous layer was extracted with chloroform
  10. washthe resultant solution was washed with an aqueous saturated sodium chloride solution
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was removed under reduced pressure
  13. customThe residue thus obtained
  14. customwas purified by silica gel column chromatography [eluent; chloroform:methanol=100:1]

출처 및 근거

ORD 기록
ord-9acbfea9c46541b0b352be3f44d02ce2
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08524738B2

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