Sodium Hydroxide → 5-[1-(3-Ethoxy-4-methoxy-phenyl)-propenyl]-2-methoxy-phenylamine

HRID 2378264Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378264
O.O.Cl[Sn]Cl.[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([N+:28]([O-])=O)[CH:21]=2)=[CH:18][CH3:19])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH3:7].[OH-].[Na+]>C(O)C.C(OCC)(=O)C>[CH2:6]([O:8][C:9]1[CH:10]=[C:11]([C:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([NH2:28])[CH:21]=2)=[CH:18][CH3:19])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16])[CH3:7]

Komponenten

6

Edukt 3

HCID 14798Sodium HydroxideHCID 61436Stannous chloride dihydrateHCID 692050534-[1-(3-Ethoxy-4-methoxy-phenyl)-propenyl]-1-methoxy-2-nitro-benzene

Produkt 1

HCID 692047575-[1-(3-Ethoxy-4-methoxy-phenyl)-propenyl]-2-methoxy-phenylamineAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

SnCl2.2H2O (3.98 g, 17.6 mmol) was added to a stirred suspension of (E/Z) 4-[1-(3-ethoxy-4-methoxy-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-ethoxy-4-methoxy-phenyl) -propenyl]-2-methoxy-phenylamine as a solid (0.73 g, 73% yield): mp, 108-110° C.; 1H NMR (CDCl3) δ 1.39-1.46 (m, 6H, 2CH3), 1.72-1.77 (m, 6H, 2CH3), 3.71-3.75 (bp, 4H, 2NH2), 3.83-3.90 (m, 12H, 4OCH3), 3.99-4.09 (m, 4H, 2CH2), 5.97-6.05 (m, 2H, 2CH), 6.54-6.61 (m, 12H, Ar); 13C NMR (CDCl3) δ 14.79, 15.67, 15.72, 55.45, 55.52, 55.90, 55.95, 64.21, 64.26, 109.90, 109.95, 110.97, 111.01, 112.13, 114.11, 114.80, 116.83, 117.51, 119.89, 120.35, 121.81, 121.98, 122.44, 132.86, 132.93, 135.52, 135.57, 136.28, 136.49, 141.93, 142.02, 146.25, 146.53, 147.75, 148.02, 148.34; Anal. Calcd for C19H23NO3: C, 73.82; H, 7.40; N, 4.47. Found: C, 72.57; H, 7.47; N, 4.40.

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-33594a011eb04649ab8cff04fa368f66
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470723B2

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