[Synthesis]
A. Synthesis of methyl 3-aminophenylacetate hydrochloride
Thionyl chloride (19.4 g, 165 mmol) was added slowly and dropwise to a methanolic (50 ml) suspension of 3-aminophenylacetic acid (5.0 g, 33 mmol) at 0°C and under argon protection. After the dropwise addition, the reaction mixture was gradually warmed up to room temperature and stirred continuously for 16 hours. After completion of the reaction, the solvent was removed by evaporation under reduced pressure and the resulting residue was ground with ether to give methyl 3-aminophenylacetate hydrochloride (5.3 g, 96.8% yield) as a colorless solid.
1H NMR (CDCl3) δ: 10.6 (s, 2H), 7.42 (m, 4H), 3.68 (s, 3H), 3.66 (s, 2H).
13C NMR (CDCl3) δ: 172.5, 137.3, 133.1, 131.2, 130.8, 125.9, 123.7, 53.5, 41.5. |