Methyl 3-nitrobenzoate → Benzoic acid, 3-amino-, methyl ester

Participants

Reaction Steps

A mixture of methyl 3-nitrobenzoate (18.1 g, 0.10 mmol) in ethanol/tetrahydrofuran (THF) (9:1), and 1.8 g of 10% Pd/C was hydrogenated at atmospheric pressure and ambient temperature for 24 hr. The reaction mixture was filtered through Celite (Celite is a registered trademark of the Johns-Manville Product Corporation for diatomaceous earth) and washed with ethanol. The solvent was removed in vacuo to give the title compound as a pale yellow solid (14.7 g; 97% yield) that was used without further purification in the next reaction. 1H-NMR (200 MHz; CDCl3) δ 7.43 (d, 1H, J=7.6 Hz), 7.35 (t, 1H, J=2.3 Hz), 7.25 (d, 1H, J=2.3 Hz), 7.19 (d, 1H, J=7.7 Hz), 3.89 (s, 3H), 3.7 ppm (bs, 2H).

Provenance & Evidence