Reaction #1747831

Reaction equation

dichloromethane

hydrochloride

3-aminophenylacetic acid

thionyl chloride

ethanol

→

desired compound

Yield 100.0%

3-aminophenylacetic acid ethyl ester

Yield 100.0%

Solvents

diethyl ether

Conditions

Workup

1. 1
   Otherto slowly rise to rt
2. 2
   OtherEvaporation of the volatiles
3. 3
   Othergave a beige solid
4. 4
   Filtrationfiltered
5. 5
   Otherto remove diethyl sulphite
6. 6
   OtherRecrystallization from dietyl ether

Procedure

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