Methyl 5-nitro-2-furoate → Methyl 5-aminofuran-2-carboxylate

Participants

Reaction Steps

A mixture of methyl 5-nitro-2-furoate (13 g, 76 mmol) and 10% Pd/C (1.3 g) in ethanol (150 mL) was shaken under an atmosphere of hydrogen at 40 psi for 18 h. The reaction mixture was filtered through diatomaceous earth and concentrated under reduced pressure to afford a crude oil. Purification by flash column chromatography (silica, 1:1 hexanes/ethyl acetate) provided methyl 5-amino-2-furoate (5.6 g): 1H NMR (500 MHz, CDCl3) δ 7.11–7.10 (m, 1H), 5.31–5.29 (m, 1H), 4.31 (br s, 2H), 3.84 (s, 3H).

Provenance & Evidence