Yield:141772-31-8 86%

Reaction Conditions:

with palladium 10% on activated carbon;hydrogen in ethyl acetate; under 760.051 Torr; for 12 h;Reflux;

Steps:

4.1.12 Preparation of methyl 5-amino-2-chloro-4-fluorobenzoate (10)

A solution of 2-chloro-4-fluoro-5-nitrobenzoic acid (13.2g, 60mmol), CH₃OH (100mL), and H₂SO₄ (0.5mL) was heated to reflux for 6h and then cooled to 25°C. Then, 200mL of ethyl acetate and H₂O (300mL) were added to the reaction solution. The ethyl acetate layer was separated and washed with saturated Na₂CO₃ solution and brine. The solution was dried using anhydrous Na₂SO₄ and filtered. 10% Pd/C (0.5g) was then added carefully to the solution, and the mixture was hydrogenated at 1atm for 12h. After the reaction was completed, it was filtrated, and the solvent was removed using rotary evaporation to give 10 (10.5g, 86%). ¹H NMR (400MHz, CDCl₃) δ 7.32 (d, J=9.2Hz, 1H), 7.10 (d, J=10.4Hz, 1H), 3.90 (s, 3H

References:

Liang, Lu;Yu, Shuyi;Li, Qian;Wang, Xia;Wang, Dawei;Xi, Zhen [Bioorganic and Medicinal Chemistry,2021,vol. 39,art. no. 116165]