7-Nitro-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester → 7-Amino-1,2,4,5-tetrahydro-benzo[d]azepine-3-carboxylic acid ethyl ester

Participants

Reaction Steps

Into a Parr hydrogenation bottle, the product from step (a) (17 g) dissolved in EtOAc (200 ml) was added. To the Ar purged bottle 10% Pd—C (1.7 g) was added. The reaction mixture was shaken under hydrogen (50 psi) for 3 hours. The reaction mixture was filtered through celite and solvent evaporated in vacuo to give the sub-title compound as an off-white solid (12.9 g). 1H NMR (300 MHz, CDCl3) δ 6.77 (d, J=7.8 Hz, 1H); 6.35 (s, 1H); 6.30 (d, J=8.1 Hz, 1H); 4.84 (s, 2H); 4.06 (q, J=6.9 Hz, 2H); 3.43 (bs, 4H); 2.66 (bs, 4H); 1.19 (t, 7.2 Hz, 3H). MS: ESI (positive): 235 (M+H).

Provenance & Evidence