Hydrochloric Acid → Ethyl 3-(3-Aminophenyl)propionate

HRID 129805

Reaktionsgleichung

Reaktionsgleichung von HRID 129805
[N+:1]([C:4]1[CH:5]=[C:6](/[CH:10]=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.Cl>[Pd].C(O)C>[NH2:1][C:4]1[CH:5]=[C:6]([CH2:10][CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:7]=[CH:8][CH:9]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 5354248Ethyl 3-nitrocinnamate

Produkt 1

HCID 82314Ethyl 3-(3-Aminophenyl)propionateAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A Parr hydrogenation vessel was charged with Part (1) compound (12.0 g, 54.3 mmol), concentrated HCl (15 mL, 0.15 mmol), 10% palladium on carbon (750 mg) and absolute ethanol (75 mL). The slurry was purged with nitrogen and agitated under an initial pressure of 45 psi of hydrogen gas. After 16 h, the flask was evacuated and the contents filtered through Celite and evaporated. The residue was dissolved in water and adjusted to pH 9 with solid sodium carbonate. The resulting mixture was extracted with dichloromethane (250 mL×2). The combined extracts were evaporated to give the title compound (8.7 g, 86%) as an oil.

Aufarbeitung

  1. customThe slurry was purged with nitrogen
  2. customthe flask was evacuated
  3. filtrationthe contents filtered through Celite
  4. customevaporated
  5. dissolutionThe residue was dissolved in water
  6. extractionThe resulting mixture was extracted with dichloromethane (250 mL×2)
  7. customThe combined extracts were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-f9564aac3fb242d79591afe53504be2c
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470845

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