Water → 1-methyl-1H-indazol-6-ol

HRID 1777115

Reaktionsgleichung

Reaktionsgleichung von HRID 1777115
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8](N)[CH:9]=2)[CH:4]=[N:3]1.N([O-])=[O:13].[Na+].O.C([O-])(O)=O.[Na+]>O.OS(O)(=O)=O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([OH:13])[CH:9]=2)[CH:4]=[N:3]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 8404331-methyl-1H-indazol-6-amineHCID 23668193Sodium Nitrite

Produkt 1

HCID 1355032231-methyl-1H-indazol-6-ol

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21910475Sulfuric acid hydrate (1:1)Lösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To a solution of 1-methyl-1H-indazol-6-amine (300 mg, 2.04 mmol) in H2O/H2SO4=1:1 (5 ml) was added NaNO2 (141 mg, 2.04 mmol) at 0° C. The mixture was then stirred for 2 h at 25° C. before being added to water (0.5 ml) and stirred for a further 2 h at 120° C. Once the reaction was complete by TLC, the mixture was treated with NaHCO3 until pH=7. The mixture was then extracted with ethyl acetate (2×10 ml) and the organic layer washed with brine (20 ml), dried over Na2SO4 and concentrated to give 1-methyl-1H-indazol-6-ol as a red solid which was used in the next step without further purification (300 mg, 99.0%). LCMS (m/z):149.1 (M+1).

Aufarbeitung

  1. stirringstirred for a further 2 h at 120° C
  2. extractionThe mixture was then extracted with ethyl acetate (2×10 ml)
  3. washthe organic layer washed with brine (20 ml)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-112fdb30df964db7a83922749d57d180
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09266836B2

Verknüpfte Notizen

Wird geladen…