Reaktion #86843

Reaktionsgleichung

hydrochloric acid

Triethylamine

2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride

ethyl 2-chloro-2-oxoacetate

sodium hydroxide

→

2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acid

Ausbeute 81.0%

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter addition
2. 2
   Waschenwashed with an aqueous solution of sodium carbonate
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   workup.ADDITIONEthanol (2 mL) and water (7.5 mL) were added to the resulting residue
6. 6
   workup.STIRRINGThe mixture was stirred at room temperature for 20 minutes
7. 7
   SonstigeThe precipitate was collected
8. 8
   workup.DISSOLUTIONwas dissolved in ethyl acetate
9. 9
   TrocknenThe ethyl acetate layer was dried over magnesium sulfate
10. 10
    Sonstigewas evaporated to dryness

Vorschrift

Triethylamine (2.28 mL; 16.22 mmol) was added to the mixture of 2-(5-chloro-1H-indol-3-yl)ethanamine hydrochloride (1.53 g; 6.49 mmol) and ethyl 2-chloro-2-oxoacetate (0.815 mL; 7.14 mmol) in dichloromethane (50 mL) at 0° C. After addition, the mixture was stirred at room temperature for 30 minutes and washed with an aqueous solution of sodium carbonate, dried over magnesium sulfate, and concentrated under reduced pressure. Ethanol (2 mL) and water (7.5 mL) were added to the resulting residue, followed by a 2M solution of sodium hydroxide (9.5 mL, 19 mmol). The mixture was stirred at room temperature for 20 minutes and the pH of the solution was adjusted to 1 by addition of a 6N hydrochloric acid. The precipitate was collected, and was dissolved in ethyl acetate. The ethyl acetate layer was dried over magnesium sulfate and was evaporated to dryness to give 1.36 g (81%) of 2-(2-(5-chloro-1H-indol-3-yl)ethylamino)-2-oxoacetic acid as a yellowish solid.

Quelle