Methyl 2-methyl-5-nitrobenzoate → Methyl 5-Amino-2-methylbenzoate

Participants

Reaction Steps

A solution of 2-methyl-5-nitro-benzoic acid methyl ester (1.50 g, 7.8 mmol) in 4:1 MeOH/EtOAc (20 mL) was shaken at room temperature with a suspension of 10% Pd/C (175 mg, 0.17 mmol) under hydrogen atmosphere (35 psi) for 17 h. The catalyst was removed by filtration over celite, and the filtrate was concentrated in vacuo to give a pale yellow oil (1.29 g, 99%). 1H NMR (CDCl3) δ 2.46 (s, 3H), 3.63 (br s, 2H), 3.87 (s, 3H), 6.74 (dd, 1H, J=9.0, 3.0 Hz), 7.02 (d, 1H, J=6.0 Hz), 7.25 (d, 1H, J=3.0 Hz).

Provenance & Evidence