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

HRID 1947788Notes

Reaction equation

HRID 1947788 reaction equation
[CH3:1][P:2](=[O:14])([CH3:13])[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([N+:10]([O-])=O)[CH:5]=1>CO.[Pd]>[CH3:13][P:2]([CH2:3][C:4]1[CH:5]=[C:6]([CH:7]=[CH:8][CH:9]=1)[NH2:10])([CH3:1])=[O:14]

Participants

4

Reactant 1

HCID 67256329Dimethyl(3-nitrobenzyl)phosphane oxide

Product 1

HCID 672538473-[(Dimethylphosphoryl)methyl]anilineYield 97.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

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, 6H), 3.06 (d, J=15.6 Hz, 2H), 3.81 (s, br, 2H), 6.55-6.58 (m, 3H), 7.08 (t, J=7.6 Hz, 1H). MS (ES+): m/z 184.02 (MH+). HPLC: tR=0.58 and 0.90 min (ZQ3, polar—5 min).

Workup

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

Sources & evidence

ORD record
ord-ef67df187b9649c48397c094024b5726
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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