Reaction #944

Reaction equation

2-aminobutyric acid

thionyl chloride

diethyl ether

→

desired product

Ethyl 2-aminobutyrate hydrochloride

Solvents

ethanol

Conditions

Workup

1. 1
   Temperaturegradually warmed to room temperature
2. 2
   TemperatureThe resulting white slurry was heated
3. 3
   Temperatureunder reflux for 3 hours
4. 4
   workup.WAITleft
5. 5
   Temperatureto cool for 10 minutes
6. 6
   workup.ADDITIONpoured
7. 7
   workup.STIRRINGwith hand stirring
8. 8
   FiltrationThe suspension was filtered
9. 9
   Otherthe solid product dried

Procedure

A slurry of 2-aminobutyric acid (100 g, Aldrich) in absolute ethanol (300 ml) was stirred under nitrogen at 0° C. and thionyl chloride (120.8 g) was added dropwise. The reaction was stirred overnight at 0° C. and then gradually warmed to room temperature. The resulting white slurry was heated under reflux for 3 hours, left to cool for 10 minutes, then poured into chilled diethyl ether (600 ml), with hand stirring. The suspension was filtered and the solid product dried to give the desired product (150 g) as a white solid. 1H NMR consistent with proposed structure.

Source