Ammonium formate → 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine

HRID 1269874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1269874
[CH3:1][C:2]1[C:10]([N+:11]([O-])=O)=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[CH3:1][C:2]1[C:10]([NH2:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:14]1[CH2:19][CH2:18][CH2:17][CH2:16][O:15]1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formateHCID 694285754-methyl-5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazole

Produkt 1

HCID 694312064-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amineAusbeute 101,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of 4-methyl-5-nitro-1-tetrahydro-2H-pyran-2-yl-1H-indazole (1.06 g, 4.06 mmol) in ethanol (20 ml) were added 10% Pd—C (200 mg) and ammonium formate (1.28 g, 20.3 mmol), and the resulting mixture was heated under reflux for 1 hour. After the solid was removed by filtration using Celite, water, ethyl acetate and a saturated aqueous sodium hydrogencarbonate solution were added to the residue. The resulting mixture was extracted with ethyl acetate, and the extract solution was washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate, and then distilled under reduced pressure to remove the solvent, whereby 4-methyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-amine (955 mg, 100%) was obtained.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 1 hour
  3. customAfter the solid was removed by filtration
  4. additiona saturated aqueous sodium hydrogencarbonate solution were added to the residue
  5. extractionThe resulting mixture was extracted with ethyl acetate
  6. washthe extract solution was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over sodium sulfate
  8. distillationdistilled under reduced pressure
  9. customto remove the solvent

Quellen und Nachweise

ORD-Eintrag
ord-3950c0a607e04f6fa78764169b4eb585
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07199147B2

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