1-(Dimethyl-phosphinoyl)-4-nitro-benzene → 4-(Dimethylphosphoryl)aniline

Participants

Reaction Steps

The dimethyl(4-nitrophenyl)phosphane oxide) produced as described above was hydrogenated in the presence of 10% Pd/C (15 mg) in MeOH (5 mL) for 2 h. The mixture was then filtered and the filtrate concentrated in vacuo to yield 19 mg of the desired 4-(dimethylphosphoryl)aniline (yield: 86%) which was used directly in further chemistries without purification. 1H-NMR (CDCl3, 400 MHz): δ=1.67 (d, J=12.8 Hz, 6 H), 4.11 (s, br, 2 H), 6.73 (dd, J=2.0, 8.4 Hz, 2 H), 7.48 (dd, J=8.4, 11.2 Hz, 2 H). MS (ES+): m/z 170.04 (MH+). HPLC: tR=1.23 min (ZQ3, polar—5 min).

Provenance & Evidence