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Water → HCID 11486071, Verbindung

HRID 639888
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 639888
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:12][CH3:13])=[CH:9][CH:10]=2)[C:5]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[C:4]([CH3:20])[N:3]=1.[C:21]1([S:27]([OH:29])=[O:28])[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Na].O>CN(C=O)C>[CH3:13][O:12][C:8]1[CH:7]=[C:6]2[C:11](=[CH:10][CH:9]=1)[C:2]([S:27]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:29])=[O:28])=[N:3][C:4]([CH3:20])=[C:5]2[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 12057Benzenesulfinic acidHCID 5360545SodiumHCID 86041352HCID 86041352, Verbindung

Produkt 1

HCID 11486071HCID 11486071, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 1-chloro-6-methoxy-3-methyl-4-phenylisoquinoline (0.24 g) in 20 mL DMF was added benzenesulfinic acid, sodium salt dihydrate (0.60 g). The reaction was heated at 120 C overnight, then poured into water and extracted with EtOAc (3×). The combined organic solutions were washed with water (1×) and brine (1×), dried (Na2SO4) and concentrated. To a solution of the residue in 20 mL DMF was added benzenesulfinic acid, sodium salt dihydrate (0.74 g). The reaction was heated at 160 C overnight, then poured into water and extracted with EtOAc (3×). The combined organic solutions were washed with water (1×) and brine (1×), dried (Na2SO4) and concentrated. The residue was recrystallized from ethyl ether/hexanes, then further purified by flash chromatography (5% to 30% EtOAc/hexanes). A second recrystallization from ethyl ether/hexanes gave the titled compound.

Aufarbeitung

  1. temperatureThe reaction was heated at 120 C overnight
  2. extractionextracted with EtOAc (3×)
  3. washThe combined organic solutions were washed with water (1×) and brine (1×)
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated
  6. additionTo a solution of the residue in 20 mL DMF was added benzenesulfinic acid, sodium salt dihydrate (0.74 g)
  7. temperatureThe reaction was heated at 160 C overnight
  8. additionpoured into water
  9. extractionextracted with EtOAc (3×)
  10. washThe combined organic solutions were washed with water (1×) and brine (1×)
  11. dry with materialdried (Na2SO4)
  12. concentrationconcentrated
  13. customThe residue was recrystallized from ethyl ether/hexanes
  14. customfurther purified by flash chromatography (5% to 30% EtOAc/hexanes)
  15. customA second recrystallization from ethyl ether/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-f65be91f0ac8438287aa39b76350f2c3
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07691879B2

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