Nitrogen → 3-(Dipropylphosphoryl)aniline

Participants

Reaction Steps

A solution of (3-nitrophenyl)(dipropyl)phosphane oxide (0.801 g, 3.14 mmol) in MeOH (3 mL) was charged with Palladium 10% wt on activated carbon (0.17 g, 0.16 mmol) and subjected to 3 cycles of evacuation and N2 purging. After a fourth evacuation the flask was purged with H2. The reaction was stirred at rt over night. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated and purified via column chromatography to afford 329 mg of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 0.90 (t, J=7.33 Hz, 6H), 1.21-1.36 (m, 2H), 1.36-1.52 (m, 2H), 1.67-1.91 (m, 4H), 5.30 (s, 2H), 6.67 (dt, J=8.02, 1.17 Hz, 1H), 6.72-6.79 (m, 1H), 6.88-6.95 (m, 1H), 7.11 (td, J=7.71, 3.54 Hz, 1H).

Provenance & Evidence