1,3-Dimethyl-5-nitro-1h-indazole → 1,3-Dimethyl-1H-indazol-5-amine

HRID 593111Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593111
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([N+:11]([O-])=O)=[CH:8][CH:9]=2)[C:4]([CH3:14])=[N:3]1>C(O)C.[Pd]>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([NH2:11])=[CH:8][CH:9]=2)[C:4]([CH3:14])=[N:3]1

Komponenten

4

Edukt 1

HCID 2909341,3-Dimethyl-5-nitro-1h-indazole

Produkt 1

HCID 588560951,3-Dimethyl-1H-indazol-5-amineAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of 307a (crude, 2.5 mmol) in ethanol (95%, 30 mL) was added NH2NH2 water (1.25 g, 25.0 mmol), Pd/C (100 mg) under nitrogen protection. The mixture was stirred at 50° C. for 1.5 h. It was then cooled to room temperature and filtered through a pad of CELITE®. The filtrate was concentrated under reduced pressure and the residue was recrystallized from anhydrous ethanol (5 mL) to afford 307b as white solid (340 mg, 84% over two steps). MS-ESI: [M+H]+ 162.3

Aufarbeitung

  1. temperatureIt was then cooled to room temperature
  2. filtrationfiltered through a pad of CELITE®
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customthe residue was recrystallized from anhydrous ethanol (5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-5fbcf7b592064da18730c113273dff8b
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238655B2

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