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) in absolute ethanol (50 mL) was combined with palladium on carbon (10 wt %, 0.30 g) and hydrogenated under a baloon of hydrogen gas for appoximately 3 hrs. The reaction mixture was filtered through a pad of diatomaceous earth and then concentrated in vacuo to an oil which crystallized when dried under high vacuum providing 3.28 g of the title compound as a tan solid. 1H NMR (300 MHz, CDCl3) d 7.38 (d, 1H, J=8.0 Hz), 7.29 (m, 1H), 7.19 (m, 1H), 6.83 (m, 1H), 1.58 (s, 9H); low resolution MS (Cl) m/e 194 (MH+).

Provenance & Evidence