Tert-butyl 3-nitrobenzoate → tert-Butyl-3-aminobenzoate

Participants

Reaction Steps

A solution of 3-nitro-benzoic acid t-butyl ester (3.77 g, 16.9 mmol), prepared as in Intermediate 15, in absolute ethanol (50 mL) is combined with palladium on carbon (10 wt %, 0.30 g) and stirred under atmospheric hydrogen for approximately 3 hrs. The reaction mixture is filtered through a pad of diatomaceous earth and then concentrated in vacuo to an oil which crystallized when dried under high vacuum providing the title compound as a tan solid (3.28 g, 16.9 mmol). 1H NMR (300 MHz, CDCl3) δ=1.58 (s, 9H); 6.79-6.87 (m, 1H), 7.19 (t, J=8.5 Hz, 1H); 7.24-7.34 (m, 1H); 7.38 (d, J=8.0 Hz, 1H). MS (Cl): [M+H]+ =194.

Provenance & Evidence