2-Benzofurancarboxylic acid, 5-nitro-, ethyl ester → Ethyl 5-aminobenzofuran-2-carboxylate

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Ethyl 5-nitrobenzofuran-2-carboxylate (Aldrich, 8.0 g) was dissolved in a mixture of EtOH and THF, treated with 10% Pd/C (wet, Degussa type E101, Aldrich) and hydrogenated on a Parr apparatus at 35 psi for 4 h. The reaction mixture was filtered over Celite, washed with THF and EtOH and concentrated under vacuum to give crude solid product, 6.3 g which was used without purification. 1H NMR (CDCl3) 7.34-7.37 (m, 2H), 6.87 (d, 1H), 6.81 (dd, 1H), 4.41 (q, 2H, OCH2), 3.60 (broad s, 2H, NH2), 1.40 (t, 3H, OCH2CH3); m/z 206.39 [M+H]+

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