Diethyl 3-Nitrobenzylphosphonate → Diethyl 3-aminobenzylphosphonate

Participants

Reaction Steps

A solution of the diethyl(3-nitrobenzyl)phosphonate prepared as described above, in MeOH (5 mL) was hydrogenated in the presence of 10% Pd/C (100 mg) overnight. The reaction mixture was filtered and the filtrate concentrated in vacuo to afford the desired product diethyl(3-aminobenzyl)phosphonate (0.690 g; yield: 95%), which was used directly in further chemistries without purification. 1H-NMR (CDCl3, 400 MHz): δ=1.24 (t, J=7.2 Hz, 6H), 3.04 (d, J=21.6 Hz, 2H), 3.66 (s, br, 2H), 4.01 (q, J=7.2 Hz, 4H), 6.57 (d, J=8.8 Hz, 1H), 6.67-6.68 (m, 2H), 7.08 (t, J=7.6 Hz, 1H). MS (ES+): m/z 244.00 (MH+). HPLC: tR=2.24 min (ZQ3, polar—5 min).

Provenance & Evidence