Hydrochloric Acid → 3-[(E)-2-(3-aminophenyl)vinyl]pyridine

HRID 2086787Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2086787
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl.C(=O)(O)[O-].[Na+]>C(O)C.[Fe]>[NH2:1][C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 227244843-[(E)-2-(3-nitrophenyl)vinyl]pyridine

Produkt 1

HCID 157868883-[(E)-2-(3-aminophenyl)vinyl]pyridineAusbeute 39,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 3-[(E)-2-(3-nitrophenyl)vinyl]pyridine (3.64 g), iron powder (3.6 g) and hydrochloric acid (35%, 11 ml) in ethanol (30 ml) was stirred at 80° C. for 4 hours. Then the mixture was poured into aqueous sodium bicarbonate and extracted with ethyl acetate twice. The combined organic phase was washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 3-[(E)-2-(3-aminophenyl)vinyl]pyridine (1.25 g).

Aufarbeitung

  1. extractionextracted with ethyl acetate twice
  2. washThe combined organic phase was washed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-02f83fb6e64e4404a6d6a9afe55be86f
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06727245B2

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