Reaktion #216987

Reaktionsgleichung

( 1 )

(E)-3-(3-Nitrophenyl)-2-propenoic acid, ethyl ester

HCl

→

title compound

Ausbeute 86.0%

3-Aminobenzenepropanoic acid, ethyl ester

Ausbeute 86.0%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe slurry was purged with nitrogen
2. 2
   Sonstigethe flask was evacuated
3. 3
   Filtrationthe contents filtered through Celite
4. 4
   Sonstigeevaporated
5. 5
   workup.DISSOLUTIONThe residue was dissolved in water
6. 6
   ExtraktionThe resulting mixture was extracted with dichloromethane (250 mL×2)
7. 7
   SonstigeThe combined extracts were evaporated

Vorschrift

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.

Quelle