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Hydrazine hydrate (1:1) → HCID 57701032, Verbindung

HRID 1186282
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1186282
[CH2:1]([N:3]([CH:11]1[CH2:16][CH2:15][CH2:14][CH:13]([C:17]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([N+:26]([O-])=O)[CH:24]=3)[NH:19][CH:18]=2)[CH2:12]1)[C:4](=[O:10])[O:5][C:6]([CH3:9])([CH3:8])[CH3:7])[CH3:2].O.NN>CO.O.[Ni]>[NH2:26][C:23]1[CH:24]=[C:25]2[C:20](=[CH:21][CH:22]=1)[NH:19][CH:18]=[C:17]2[CH:13]1[CH2:14][CH2:15][CH2:16][CH:11]([N:3]([CH2:1][CH3:2])[C:4](=[O:10])[O:5][C:6]([CH3:7])([CH3:8])[CH3:9])[CH2:12]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 2

HCID 24654Hydrazine hydrate (1:1)HCID 57701041HCID 57701041, Verbindung

Produkt 1

HCID 57701032HCID 57701032, VerbindungAusbeute 98,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 935NickelKatalysatorHCID 887MethanolLösungsmittel
HCID 962
Water
Lösungsmittel

Versuchsvorschrift

To a solution of tert-butyl ethyl(3-(5-nitro-1H-indol-3-yl)cyclohexyl)carbamate (0.70, g 1.81 mmol) in dry MeOH (15 mL) was added Raney-Ni (0.1 g as a slurry in water) and hydrazine hydrate (0.90 mL, 18.10 mmol). The resulting mixture was immersed in a preheated oil bath and refluxed for 15 minutes or until the solution became clear. The reaction was cooled and filtered trough Celite, washed with MeOH (20 mL), and the solvent evaporated. The crude was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98) to give the title compound as a brownish solid (0.64 g, quantitative). 1H-NMR (CDCl3) δ 1.12 (t, 3H, J=6.8 Hz), 1.45 (s, 9H), 1.53-1.69 (m, 3H), 1.71-1.79 (m 1H), 1.82-1.92 (m, 1H), 2.07-2.17 (m, 2H), 3.06-3.24 (m, 2H), 3.43-3.56 (m, 1H), 4.43 (s, 1H), 6.64 (dd, 1H, J=2.1, 8.4 Hz), 6.89 (d, 1H, J=2.1 Hz), 7.15 (d, 1H, J=8.4 Hz), 7.26 (s, 1H), 7.33 (s, 1H), 7.82 (s, 1H); EI-MS (m/z, %) 357 (M+, 70), 212 (100).

Aufarbeitung

  1. customThe resulting mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 15 minutes or until the solution
  3. temperatureThe reaction was cooled
  4. filtrationfiltered trough Celite
  5. washwashed with MeOH (20 mL)
  6. customthe solvent evaporated
  7. customThe crude was purified on column chromatography (2 M NH3 in MeOH:CH2Cl2, 2:98)

Quellen und Nachweise

ORD-Eintrag
ord-76d514dd88414ecd8509e7ef0fa646ba
Quelldatensatz
uspto-grants-2014_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08673909B2

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