Aluminum(III) Chloride → 1-Methyl-1H-indazol-5-ol

HRID 1715584

Reaktionsgleichung

Reaktionsgleichung von HRID 1715584
C[O:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH3:12])[N:7]=[CH:6]2.[Al+3].[Cl-].[Cl-].[Cl-]>C1(C)C=CC=CC=1>[CH3:12][N:8]1[C:9]2[C:5](=[CH:4][C:3]([OH:2])=[CH:11][CH:10]=2)[CH:6]=[N:7]1

Komponenten

4

Edukt 2

HCID 6451240Aluminum(III) ChlorideHCID 574187495-Methoxy-1-methylindazole

Produkt 1

HCID 441192401-Methyl-1H-indazol-5-olAusbeute 13,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

To a solution of (2t) (0.99 g, 6.1 mmol) in toluene (30 mL) was added AlCl3 (2.44 g, 18.3 mmol) at room temperature, upon which a purple colored mixture formed. After refluxing for 20 minutes, an olive colored mixture formed. The mixture was refluxed for 2 hours, allowed to cool to room temperature and poured into an ice-water bath. The insoluble solids were collected by filtration (398 mg). The filtrate was extracted with DCM, filtered through 1PS paper, evaporated in vacuo and purified on the Biotage eluting with (1:9) then (3:7) Et2O/DCM and finally (1:1) DCM/Et2O. The product fractions were evaporated in vacuo affording compound (3t) as a brown foam (122 mg). Total combined yield, 520 mg (58%). 1H NMR (400 MHz, CDCl3) δ 7.38 (d, J=7.8 Hz, 1H), 7.17 (dd, J=7.8, 1.6 Hz, 1H), 7.13 (d, J=1.6 Hz, 1H), 5.19-5.18 (m, 1H), 4.51-4.44 (m, 1H), 4.43-4.36 (m, 1H), 2.53-2.45 (m, 1H), 2.36-2.30 (m, 1H); MS (ESI+) m/z 149 (M+H) detected.

Aufarbeitung

  1. customupon which a purple colored mixture formed
  2. temperatureAfter refluxing for 20 minutes
  3. customan olive colored mixture formed
  4. temperatureThe mixture was refluxed for 2 hours
  5. additionpoured into an ice-water bath
  6. filtrationThe insoluble solids were collected by filtration (398 mg)
  7. extractionThe filtrate was extracted with DCM
  8. filtrationfiltered through 1PS paper
  9. customevaporated in vacuo
  10. custompurified on the Biotage
  11. washeluting with (1:9)
  12. customThe product fractions were evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-dcab0eeedec74d30ba182689668a9ada
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799782B2

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