Diethyl 3-Nitrobenzylphosphonate → Diethyl 3-aminobenzylphosphonate

HRID 1947783Notes

Reaction equation

HRID 1947783 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([N+:16]([O-])=O)[CH:11]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>CO.[Pd]>[CH2:6]([O:5][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([NH2:16])[CH:11]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

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, 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).

Workup

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

Sources & evidence

ORD record
ord-f7c14f47f01a4f829d223a2423065c51
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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