tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate → Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

HRID 626414Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626414
[Cl:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=[CH:4][C:3]=1[N+:17]([O-])=O>[Pd].C(OCC)(=O)C>[NH2:17][C:3]1[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=1[Cl:1]

Komponenten

4

Edukt 1

HCID 58136394tert-Butyl (2E)-3-(4-chloro-3-nitrophenyl)prop-2-enoate

Produkt 1

HCID 58136497Tert-butyl 3-(3-amino-4-chlorophenyl)propanoate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under argon, 5.4 g of 10% palladium on carbon were added to a solution of 72.0 g (254 mmol) of tert-butyl (2E)-3-(4-chloro-3-nitrophenyl)acrylate in 1.0 liters of ethyl acetate. The suspension was stirred at RT under a hydrogen atmosphere at standard pressure for 7 h. The reaction mixture was then filtered off with suction through kieselguhr, and the filtrate was concentrated. The crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 9:1). This gave 38 g (58% of theory) of the title compound.

Aufarbeitung

  1. filtrationThe reaction mixture was then filtered off with suction through kieselguhr
  2. concentrationthe filtrate was concentrated
  3. customThe crude product was purified by chromatography on silica gel (mobile phase cyclohexane/ethyl acetate 9:1)

Quellen und Nachweise

ORD-Eintrag
ord-d2f2e41eb4034c2d8e3e95067a9310b4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309198B2

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