Sodium Hydroxide → 1H-Indazol-5-ol

HRID 916453

Reaktionsgleichung

Reaktionsgleichung von HRID 916453
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6]2.B(Br)(Br)Br.[OH-].[Na+]>C(Cl)CCl.C(Cl)Cl>[OH:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][N:7]=[CH:6]2

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 133468605-Methoxy-1H-indazole

Produkt 1

HCID 1014381H-Indazol-5-olAusbeute 65 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 111,2-DichloroethaneLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Methoxyindazole (1.7 g, 11.5 mmol), (Tetrahedron, 1994, 50, 3529), was dissolved in ethylene chloride (35 ml) and cooled in an ice/water bath. Boron tribromide (57.4 ml of a 1M olution in methylene chloride, 57.4 mmol) was added over 10 minutes and then the mixture allowed to warm to ambient temperature. The mixture was stirred for 2 hours and then re-cooled in an ice/water bath. 2N Sodium hydroxide was slowly added until pH 8. The precipitated solid was filtered off and dried under vacuum at 60° C. overnight. The residue was purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 5-hydroxyindazole (1.0 g, 65%) as a brown solid.

Aufarbeitung

  1. temperaturecooled in an ice/water bath
  2. temperaturere-cooled in an ice/water bath
  3. filtrationThe precipitated solid was filtered off
  4. customdried under vacuum at 60° C. overnight
  5. customThe residue was purified by column chromatography
  6. washeluting with methylene chloride/methanol (95/5)

Quellen und Nachweise

ORD-Eintrag
ord-0deb1d7ed7794615898ae5d85b81ecde
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07268230B2

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