2-(3-Aminophenyl)acetic acid ethyl ester Chemical Properties

Boiling point:

138-140 °C(Press: 3-4 Torr)

Density 

1.112±0.06 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

4.36±0.10(Predicted)

Appearance

Brown to black Liquid

2-(3-Aminophenyl)acetic acid ethyl ester Usage And Synthesis

Synthesis

General procedure for the synthesis of ethyl 2-(3-aminophenyl)acetate from ethyl 3-nitrophenylacetate: ethyl 2-(3-nitrophenyl)acetate (3h) (1.05 g, 3.40 mmol) was dissolved in methanol (25 mL) and hydrogenation reaction was carried out for 4 h by adding 10% Pd/C (catalytic amount) as a catalyst. After completion of the reaction, the catalyst was removed by filtration and the filtrate was concentrated to afford the target product ethyl 2-(3-aminophenyl)acetate (4h). The product was characterized by 1H-NMR (200 MHz, CDCl3): δ 1.25 (t, 3H, J = 7.2 Hz), 3.51 (s, 2H), 4.14 (q, 2H, J = 7.2 Hz), 6.59-6.71 (m, 3H), 7.11 (t, 1H, J = 7.8 Hz). The reaction was carried out quantitatively in 100% yield.

References

[1] Patent: EP3381898, 2018, A1. Location in patent: Paragraph 0200; 0265
[2] Collection of Czechoslovak Chemical Communications, 1995, vol. 60, # 4, p. 659 - 669
[3] Bioorganic and Medicinal Chemistry, 2008, vol. 16, # 3, p. 1206 - 1217
[4] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 1, p. 217 - 220
[5] Patent: US6150373, 2000, A