1-{2-[2-(2-Methoxyethoxy)ethoxy]ethoxy}-4-nitrobenzene → 4-(2-(2-(2-Methoxyethoxy)ethoxy)ethoxy)aniline

Participants

Reaction Steps

To a stirred solution of 17 (1.39 g, 4.86 mmol) in acidic EtOH (5 mL) in a Parr apparatus was added a catalytic amount of 20% Pd/C (0.05 g). The reaction vessel was purged with H2 then pressurized to 70 psi. After stirring for 16 h the reaction mixture was filtered through a 4 cm pad of celite and concentrated under reduced pressure to afford 18 as a brown oil (1.24 g, 100%): 1H NMR (300 MHz, CDCl3) δ 6.75 (d, J=8.8 Hz, 2H), 6.62 (d, J=8.8 Hz, 2H), 4.11-3.99 (m, 2H), 3.87-3.78 (m, 2H), 3.76-3.51 (m, 8H), 3.42 (s, 1H), 3.38 (s, 2H).

Provenance & Evidence