Methanol → 4-Hydroxyiminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole

HRID 127517Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 127517
[C:1]1([N:7]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[C:8]2[S:16][CH2:17][CH:18]=[CH:19][CH2:20]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CO.Cl.[OH:25][NH2:26]>N1C=CC=CC=1>[OH:25][N:26]=[CH:20][CH:19]1[C:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[N:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:8]=2[S:16][CH2:17][CH2:18]1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 443297Hydroxyamine hydrochlorideHCID 544806471-Phenyl-2-(4-hydroxy-2-butenylthio)indole

Produkt 1

HCID 571160384-Hydroxyiminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indoleAusbeute 84,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

A solution of the product of the above (2) (3.71 g) in pyridine (75 ml) is heated at 110° C. for 70 minutes. After cooling, methanol (25 ml) and hydroxyamine hydrochloride (2.2 g) are added thereto. The mixture is stirred at room temperature for 50 minutes and evaporated. The residue is acidified with ice-cooled 3 N-hydrochloric acid and extracted with chloroform. The extract is evaporated to give oily residue. The residue is chromatographed on a column of silica gel and eluted with benzene. The eluate is evaporated to give 4-hydroxyiminomethyl-9-phenyl-2,3,4,9-tetrahydrothiopyrano[2,3-b]indole (3.28 g). The product is dissolved into tetrahydrofuran (55 ml) and lithium aluminium hydride (1.4 g) is added thereto at room temperature. The mixture is refluxed for 1 hour. Ethyl acetate, an 10% aqueous solution of sodium hydroxide and water are successively added thereto. The precipitate is collected by filtration, washed with ethyl acetate and chloroform, and added to the filtrate. The organic layer is separated, washed with water, dried and evaporated to give the free base of the title compound as an oil.

Aufarbeitung

  1. temperatureAfter cooling
  2. customevaporated
  3. temperaturecooled 3 N-hydrochloric acid
  4. extractionextracted with chloroform
  5. customThe extract is evaporated
  6. customto give oily residue
  7. customThe residue is chromatographed on a column of silica gel
  8. washeluted with benzene
  9. customThe eluate is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-62687872218d4e5e965dae8133184ae0
Quelldatensatz
uspto-grants-1981_03
Patentnummer
US04256640

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