Réaction #1747831

Équation de réaction

dichloromethane

hydrochloride

3-aminophenylacetic acid

thionyl chloride

ethanol

→

desired compound

Rendement 100.0%

3-aminophenylacetic acid ethyl ester

Rendement 100.0%

Solvants

diethyl ether

Conditions de réaction

Traitement

1. 1
   Autreto slowly rise to rt
2. 2
   AutreEvaporation of the volatiles
3. 3
   Autregave a beige solid
4. 4
   Filtrationfiltered
5. 5
   Autreto remove diethyl sulphite
6. 6
   AutreRecrystallization from dietyl ether

Mode opératoire

To a cooled solution (−15° C.) of 3-aminophenylacetic acid (10.2, 67 mmol) in ethanol (200 mL) was added dropwise thionyl chloride (10 mL, 0.14 mol). The reaction mixture was stirred for 24 h allowing the temperature to slowly rise to rt. Evaporation of the volatiles gave a beige solid that was stripped several times with dichloromethane. The solid was then treated with hot diethyl ether and filtered to remove diethyl sulphite. Recrystallization from dietyl ether gave 14.4 g, 67 mmol, 100% of the desired compound as an off-white crystalline hydrochloride, mp 135° C. IR (KBr) cm−1 2857,2614, 1740

Source