1-(Dimethyl-phosphinoyl)-4-nitro-benzene → 4-(Dimethylphosphoryl)aniline

HRID 511217Notes

Reaction equation

HRID 511217 reaction equation
[CH3:1][P:2](=[O:13])([CH3:12])[C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-])=O)=[CH:5][CH:4]=1>CO.[Pd]>[CH3:12][P:2]([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)([CH3:1])=[O:13]

Participants

4

Reactant 1

HCID 218979121-(Dimethyl-phosphinoyl)-4-nitro-benzene

Product 1

HCID 206345534-(Dimethylphosphoryl)anilineYield 86%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The dimethyl(4-nitrophenyl)phosphane oxide) produced as described above was hydrogenated in the presence of 10% Pd/C (15 mg) in MeOH (5 mL) for 2 h. The mixture was then filtered and the filtrate concentrated in vacuo to yield 19 mg of the desired 4-(dimethylphosphoryl)aniline (yield: 86%) which was used directly in further chemistries without purification. 1H-NMR (CDCl3, 400 MHz): δ=1.67 (d, J=12.8 Hz, 6 H), 4.11 (s, br, 2 H), 6.73 (dd, J=2.0, 8.4 Hz, 2 H), 7.48 (dd, J=8.4, 11.2 Hz, 2 H). MS (ES+): m/z 170.04 (MH+). HPLC: tR=1.23 min (ZQ3, polar—5 min).

Workup

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

Sources & evidence

ORD record
ord-48273612fb02420ca52532033344a475
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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