Methyl 3-(4-nitrophenyl)-2-propenoate → Methyl 3-(4-aminophenyl)propanoate

HRID 386436

Reaktionsgleichung

Reaktionsgleichung von HRID 386436
[N+:1]([C:4]1[CH:9]=[CH:8][C:7](/[CH:10]=[CH:11]/[C:12]([O:14][CH3:15])=[O:13])=[CH:6][CH:5]=1)([O-])=O>CO.C1COCC1.[Pd]>[NH2:1][C:4]1[CH:5]=[CH:6][C:7]([CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:9]=1

Komponenten

5

Edukt 1

HCID 5354137Methyl 3-(4-nitrophenyl)-2-propenoate

Produkt 1

HCID 417374Methyl 3-(4-aminophenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

A solution of methyl (E)-3-(4-nitrophenyl)acrylate (S31, 4.10 g, 19.8 mmol) in MeOH (30 mL) and THF (30 mL) was treated with 10% Pd/C (400 mg). The reaction mixture was purged with H2 and was stirred at 25° C. for 10 h. The suspension was filtered through diatomaceous earth and concentrated to afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid: 1H NMR (CDCl3, 500 MHz) 6.99 (d, 2H, J=8.2 Hz), 6.63 (d, 2H, J=8.4 Hz), 3.60 (s, 3H), 2.85 (t, 2H, J=7.7 Hz), 2.58 (t, 2H, J=7.7 Hz); 13C NMR (CDCl3, 125 MHz) 173.5, 144.6, 130.5, 129.1, 115.3, 51.5, 36.1, 30.1.

Aufarbeitung

  1. customThe reaction mixture was purged with H2
  2. filtrationThe suspension was filtered through diatomaceous earth
  3. concentrationconcentrated
  4. customto afford S32 (3.40 g, 19.0 mmol, 95%) as a yellow solid

Quellen und Nachweise

ORD-Eintrag
ord-77a0dd304c9441dd91cb47a29775c16c
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08372823B2

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