Stannous Chloride → 2-Benzyloxy-6-methylaniline

HRID 660828

Reaktionsgleichung

Reaktionsgleichung von HRID 660828
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[N+:16]([O-])=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[Sn]Cl>CCOC(C)=O>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[C:10]=1[NH2:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 24479Stannous ChlorideHCID 33441871-Benzyloxy-3-methyl-2-nitrobenzene

Produkt 1

HCID 27629472-Benzyloxy-6-methylaniline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a stirred solution of 1-benzyloxy-3-methyl-2-nitrobenzene (5.0 g, 20.6 mmol) in EtOAc (150 mL) is added SnCl2 (23.2 g, 103 mmol) and the suspension is heated at 80° C. overnight. The suspension is filtered and the filtrate washed with sat. NaHCO3 and extracted with EtOAc. The combined organic layers are washed with water, brine, then dried over MgSO4 and filtered. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1) to give the title compound as a yellow oil.

Aufarbeitung

  1. filtrationThe suspension is filtered
  2. washthe filtrate washed with sat. NaHCO3
  3. extractionextracted with EtOAc
  4. washThe combined organic layers are washed with water, brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customThe solvent is removed under reduced pressure
  8. customthe residue is purified by flash chromatography (hexanes/EtOAc=10:1 to 5:1)

Quellen und Nachweise

ORD-Eintrag
ord-497302fff055418384eab6c259e66d60
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08084448B2

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