Dimethyl(3-nitrobenzyl)phosphane oxide → 3-[(Dimethylphosphoryl)methyl]aniline

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Reaction Steps

The dimethyl(3-nitrobenzyl)phosphane oxide (153 mg) produced as described above was hydrogenated in the presence of 10% Pd/C (100 mg) in MeOH (5 mL) overnight. The mixture was filtered and the filtrate concentrated in vacuo to afford 128 mg of the desired 3-[(dimethylphosphoryl)methyl]aniline (yield: 96%), which was used in further chemistries without purification. 1H-NMR (CDCl3, 400 MHz): δ=1.44 (d, J=12.8 Hz, 6 H), 3.06 (d, J=15.6 Hz, 2 H), 3.81 (s, br, 2 H), 6.55-6.58 (m, 3 H), 7.08 (t, J=7.6 Hz, 1 H). MS (ES+): m/z 184.02 (MH+). HPLC: tR=0.58 and 0.90 min (ZQ3, polar—5 min).

Provenance & Evidence