5-Nitro-3-phenyl-1H-indazole → 3-Phenyl-1H-indazol-5-amine

HRID 1272732

Reaktionsgleichung

Reaktionsgleichung von HRID 1272732
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][N:8]=[C:7]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Komponenten

4

Edukt 1

HCID 6174445-Nitro-3-phenyl-1H-indazole

Produkt 1

HCID 224801043-Phenyl-1H-indazol-5-amineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A suspension of 5-nitro-3-phenyl-1H-indazole (0.239 g, 1.0 mmol) and palladium (10 wt % on activated carbon, 30 mg) in ethyl acetate (10 mL) was stirred under hydrogen at ambient temperature for 18 hours. It was filtered with celite and washed with ethyl acetate. The filtrate was concentrated and the residue was then purified by chromatography (SiO2, 30–50% ethyl acetate/hexane) to provide the title compound (0.184 g, 88% yield): mp 104° C.; 1H NMR (CDCl3) δ 10.40 (br s, 1H), 7.94 (d, 2H), 7.51 (m, 2H), 7.20–7.42 (m, 3H), 6.90 (m, 1H), 3.6 (br, 2H); EI-MS (m/z) 209 [M]+.

Aufarbeitung

  1. filtrationIt was filtered with celite
  2. washwashed with ethyl acetate
  3. concentrationThe filtrate was concentrated
  4. customthe residue was then purified by chromatography (SiO2, 30–50% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f229d86b9cb7419fb9d0b87e204e3d62
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07208513B2

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