Ammonium Hydroxide → 7-Methoxynaphthalen-2-amine

Participants

Reaction Steps

The solution of 7-methoxynaphthalen-2-ol (6.5 g, 37.31 mmol) and NaHSO3 (11.6 g, 111.54 mmol) in ammonium hydroxide (100 ml) was stirred for 2 days at 140° C. in a sealed tube and then cooled to room temperature. The solids were collected by filtration to afford 7-methoxynaphthalen-2-amine as an off-white solid (4.5 g, 70%). (ES, m/z): [M+H]+ 174.1; 1H NMR (300 MHz, CDCl3): δ 7.57 (d, J=8.7 Hz, 2H), 6.97-6.87 (m, 3H), 6.79 (dd, J=8.7, 2.1 Hz, 1H), 3.90 (s, 3H), 3.84 (br s, 2H).

Provenance & Evidence