Diethyl 3-Nitrobenzylphosphonate → Diethyl 3-aminobenzylphosphonate

HRID 511210Notes

Reaction equation

HRID 511210 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][P:8](=[O:15])([O:12][CH2:13][CH3:14])[O:9][CH2:10][CH3:11])([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([CH:16]=[CH:17][CH:18]=1)[CH2:7][P:8](=[O:15])([O:9][CH2:10][CH3:11])[O:12][CH2:13][CH3:14]

Participants

4

Reactant 1

HCID 13675396Diethyl 3-Nitrobenzylphosphonate

Product 1

HCID 19077611Diethyl 3-aminobenzylphosphonateYield 95%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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, 2 H), 3.66 (s, br, 2 H), 4.01 (q, J=7.2 Hz, 4 H), 6.57 (d, J=8.8 Hz, 1 H), 6.67-6.68 (m, 2 H), 7.08 (t, J=7.6 Hz, 1 H). MS (ES+): m/z 244.00 (MH+). HPLC: tR=2.24 min (ZQ3, polar—5 min).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-e85084a330774522af31453fd3205d79
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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