Stannous Chloride → N-(2-aminophenyl)-N-cyclohexylamine

HRID 220815Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 220815
[CH:1]1([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Sn](Cl)Cl>CO>[CH:1]1([NH:7][C:8]2[C:9]([NH2:14])=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 3101179N-cyclohexyl-2-nitroaniline

Produkt 1

HCID 1517328N-(2-aminophenyl)-N-cyclohexylamineAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Cyclohexyl-(2-nitro-phenyl)-amine from Example E26.1 (3.0 g, 13.6 mmol) was dissolved in methanol (100 ml) and tin (II) chloride (12.9 g, 68.1 mmol) was added. The mixture was stirred for 20 h at room temperature then heated at reflux for 18 h and concentrated in vacuo. The residue was placed in EtOAC (100 ml), cooled down to 0° C. and pH was adjusted to 14 with conc. NH3. The precipitate was filtered off and washed with EtOAc. The filtrate was washed with 2M NH3, water then brine, dried and concentrated in vacuo to yield the title compound (2.25 g, 86%).

Aufarbeitung

  1. temperaturethen heated
  2. temperatureat reflux for 18 h
  3. concentrationconcentrated in vacuo
  4. temperaturecooled down to 0° C.
  5. filtrationThe precipitate was filtered off
  6. washwashed with EtOAc
  7. washThe filtrate was washed with 2M NH3, water
  8. dry with materialbrine, dried
  9. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-1f7589b840c24eaab392de25166d05a7
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202858B2

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