4-Bromo-2-nitroaniline → 4-Bromobenzene-1,2-diamine

Participants

Reaction Steps

4-Bromo-2-nitroaniline (12 g, 55 mmol), 1% Pt/C (1.2 g) and THF (120 mL) were added to a 250 mL bottle. The reaction mixture was hydrogenated at a pressure of approximately 40 psig H2. The hydrogenation reaction mixture was monitored by HPLC until the Area % of 4-bromo-2-nitroaniliine was less than 1%. The reaction mixture was filtered and then concentrated to yield 10.6 g of 4-bromo-benzene-1,2-diamine (as a black oil that solidifies). 4-Bromo-benzene-1,2-diamine was used in the next step without further purification. 1H NMR (400 MHz, CDCl3) δ 3.28 (br, 4H), 6.54 (d, 1H), 6.77-6.81 (m, 2H).

Provenance & Evidence