Methyl 3-(benzyloxy)-4-nitrobenzoate → Methyl 4-amino-3-(benzyloxy)benzenecarboxylate

Participants

Reaction Steps

To a tetrahydrofuran solution (100 mL) of 3-benzyloxy-4-nitro-benzoic acid methyl ester(10.0 g, 34.9 mmol) was added Raney Nickel (wet) (2.0 g). The reaction was pressured to approximately 50 psi at left to shake at room temperature for 5.5 h. An aliquot was removed and TLC deemed the reaction complete. The reaction was filtered through celite and then concentrated under reduced pressure to yield 4-amino-3-benzyloxy-benzoic acid methyl ester as a solid (8.7 g, 97%). 1H NMR (CDCl3) 7.58(m,2H), 7.50-7.30(m,5H), 6.70(d,1H), 5.14(s,2H), 4.84(s,3H).

Provenance & Evidence