Benzoic acid, 4-amino-3-(1-methylethoxy)-, methyl ester (9CI)

159783-41-2

681465-85-0

Methyl 3-isopropoxy-4-nitrobenzoate (2.60 g, 10.87 mmol) was dissolved in methanol (91.0 mL) and degassed. A 10% palladium/carbon catalyst (0.58 g, 0.54 mmol) was added and a vacuum was applied under cooling conditions to remove air. After rinsing the reaction flask with hydrogen, the suspension was stirred at room temperature for 17 hours. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration and washed with methanol. The solvent was removed by concentration under reduced pressure to give the crude product. The crude product was purified by fast column chromatography (petroleum ether/ethyl acetate = 7/3) to afford methyl 3-isopropoxy-4-aminobenzoate (2.27 g, 10.85 mmol, quantitative yield) as a light orange solid. Melting point: 55-57 °C. 1H NMR (400 MHz, CDCl3) δ 7.51 (dd, J = 8.2, 1.7 Hz, 1H), 7.46 (d, J = 1.7 Hz, 1H), 6.66 (dd, J = 8.2, 5.1 Hz, 1H), 4.63 (sept, J = 5.1 Hz, 1H), 3.85 (s, 3H), 1.36 (s, 3H), 1.36 (s, 3H). 1.36 (s, 3H), 1.35 (s, 3H) ppm.13C NMR (100 MHz, CDCl3) δ 167.5, 144.24, 142.3, 124.0, 119.5, 114.1, 113.5, 70.9, 51.8, 22.3 ppm.HRMS (ESI): calculated values C11H16NO3 ( M + H)+: 210.1130, measured value: 210.1126.