Heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide → Heptanoic acid [2-(4-amino-phenyl)-ethyl]-amide

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Reaction Steps

1H NMR (400 MHz, CDCl3) δ8.16 (d, 2H), 7.35 (d, 2H), 5.43 (s, 1H), 3.54 (m, 2H), 2.93 (t, 2H), 2.12 (t, 2H), 1.57 (m, 3H), 1.26 (m, 5H), 0.86 (t, 3H). 10% Palladium on carbon (380 mg, 10 wt %) was added to a solution of heptanoic acid [2-(4-nitro-phenyl)-ethyl]-amide (3.80 g, 13.6 mmol) and methanol (80 mL) in a Parr bottle and the resulting mixture hydrogenated at 55 psi for 4 h. The reaction mixture was filtered through a plug of Celite and the Celite plug washed thoroughly with ethyl acetate. The combined filtrates were concentrated under reduced pressure to provide 3.24 g (96%) of heptanoic acid [2-(4-amino-phenyl)-ethyl]-amide as an off-white solid.

Provenance & Evidence