Sodium Hydroxide → 5-[1-(3,5-Dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine

HRID 2378266Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378266
O.O.Cl[Sn]Cl.[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([N+:27]([O-])=O)[CH:20]=2)=[CH:17][CH3:18])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1.[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[CH3:6][O:7][C:8]1[CH:9]=[C:10]([C:16]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[C:21]([NH2:27])[CH:20]=2)=[CH:17][CH3:18])[CH:11]=[C:12]([O:14][CH3:15])[CH:13]=1

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 692040644-[1-(3,5-Dimethoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene

Produkt 1

HCID 692036045-[1-(3,5-Dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamineAusbeute 66,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

SnCl2.2H2O (5.20 g, 23.0 mmol) was added to a stirred solution of (E/Z) 4-[1-(3,5-dimethoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene (1.10 g, 3.2 mmol) in ethanol (200 proof, 20 mL) and ethyl acetate (10 mL). The reaction mixture was heated at 70° C. for 1 h. The solution was cooled down to room temperature, poured into ice water (100 mL), and basified with 10 N NaOH (20 mL) to pH ˜12. The aqueous layer was extracted with ethyl acetate (5×35 mL). The combined organic layers were washed with water (60 mL), brine (50 mL) and dried (MgSO4). Removal of solvent and chromatography (Silica Gel) gave a mixture of (E/Z) 5-[1-(3,5-dimethoxy-phenyl)-propenyl]-2-methoxy-phenylamine as an oil (0.64 g, 51% yield): 1H NMR (CDCl3) δ 1.70-1.78 (2d, J=7.0 Hz, 6H, 2CH3), 3.74-3.87 (4s+m, 22H, 6OCH3+2NH2), 6.02-6.10 (m, 2H, 2CH), 6.33-6.79 (m, 12H, Ar); 13C NMR (CDCl3) δ 15.60, 15.73, 55.30, 55.45, 55.52, 98.70, 98.92, 105.72, 107.99, 109.95, 109.99, 113.91, 116.77, 117.30, 120.32, 122.05, 123.83, 132.49, 135.56, 135.61, 142.09, 142.33, 142.50, 145.66, 146.32, 146.56, 160.36, 160.51; Anal. Calcd for C18H21NO3: C, 72.22; H, 7.07; N, 4.68. Found: C, 71.94; H, 7.37; N, 4.54.

Aufarbeitung

  1. temperatureThe solution was cooled down to room temperature
  2. extractionThe aqueous layer was extracted with ethyl acetate (5×35 mL)
  3. washThe combined organic layers were washed with water (60 mL), brine (50 mL)
  4. dry with materialdried (MgSO4)
  5. customRemoval of solvent and chromatography (Silica Gel)
  6. customgave

Quellen und Nachweise

ORD-Eintrag
ord-f74be3d125824eb18db6da8bb9946212
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470723B2

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