HCID 54039567, Verbindung → 3-(3,4-Dimethoxyphenyl)-3-(3-aminophenyl)acrylonitrile

HRID 366609Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 366609
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([N+:21]([O-])=O)[CH:16]=2)=[CH:12][C:13]#[N:14])[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].[H][H]>C(OCC)(=O)C.[Pd]>[NH2:21][C:17]1[CH:16]=[C:15]([C:11]([C:5]2[CH:6]=[CH:7][C:8]([O:9][CH3:10])=[C:3]([O:2][CH3:1])[CH:4]=2)=[CH:12][C:13]#[N:14])[CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 2

HCID 54039567HCID 54039567, VerbindungHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 537858693-(3,4-Dimethoxyphenyl)-3-(3-aminophenyl)acrylonitrileAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of 3-(3,4-dimethoxyphenyl)-3-(3'-nitrophenyl)acrylonitrile (0.7 g, 2.3 mmol) in 40 mL of ethyl acetate was added 0.1 g of 10% palladium on carbon catalyst. The mixture was hydrogenated in a Parr-Shaker apparatus at 55-60 psi of hydrogen for 2.5 hours. The reaction mixture was filtered through celite and the filtrate was concentrated in vacuo to afford the crude product. The crude product was purified by flash column chromatography (silica gel, 15% ethyl acetate/methylene chloride) to afford 0.25 g (56%) of a mixture of the E and Z isomers as a yellow solid: mp 100-101° C.; 1H NMR (CDCl3) δ 7.30-6.59 (m, 14 H); 5.63 (s, 1 H), 5.59 (s, 1 H), 3.94 (s, 3 H), 3.91 (s, 3 H), 3.87 (s, 3 H), 3.84 (s, 3 H); 13C NMR (CDCl3) δ 163.1, 162.9, 151.1, 150.5, 148.8, 148.7, 146.5, 146.4, 140.4, 138.2, 131.5, 129.5, 129.5, 129.4, 123.2, 122.1, 119.9, 119.0, 118.4, 118.2, 116.8, 116.6, 115.9, 115.0, 112.7, 111.0, 110.7, 93.3, 92.7, 56.1, 56.0, 55.9; Anal. Calcd for C17H16N2O3. Theoretical: C, 72.84; H, 5.75; N, 9.99. Found: C, 72.48; H, 6.05; N, 9.58.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto afford the crude product
  4. customThe crude product was purified by flash column chromatography (silica gel, 15% ethyl acetate/methylene chloride)

Quellen und Nachweise

ORD-Eintrag
ord-2f3f24aff88042ac9c2484db95167804
Quelldatensatz
uspto-grants-2000_10
Patentnummer
US06130226

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