Nitrogen → 3-(Dipropylphosphoryl)aniline

HRID 1947966Notes

Reaction equation

HRID 1947966 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([P:10](=[O:17])([CH2:14][CH2:15][CH3:16])[CH2:11][CH2:12][CH3:13])[CH:7]=[CH:8][CH:9]=1)([O-])=O.N#N>CO.[Pd]>[CH2:11]([P:10]([C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[NH2:1])([CH2:14][CH2:15][CH3:16])=[O:17])[CH2:12][CH3:13]

Participants

5

Reactant 2

HCID 947NitrogenHCID 67254248(3-Nitrophenyl)(dipropyl)phosphane oxide

Product 1

HCID 672552723-(Dipropylphosphoryl)anilineYield 46.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of (3-nitrophenyl)(dipropyl)phosphane oxide (0.801 g, 3.14 mmol) in MeOH (3 mL) was charged with Palladium 10% wt on activated carbon (0.17 g, 0.16 mmol) and subjected to 3 cycles of evacuation and N2 purging. After a fourth evacuation the flask was purged with H2. The reaction was stirred at rt over night. The reaction mixture was filtered through a pad of celite and the filtrate was concentrated and purified via column chromatography to afford 329 mg of the desired product. 1H NMR (400 MHz, DMSO-d6) δ 0.90 (t, J=7.33 Hz, 6H), 1.21-1.36 (m, 2H), 1.36-1.52 (m, 2H), 1.67-1.91 (m, 4H), 5.30 (s, 2H), 6.67 (dt, J=8.02, 1.17 Hz, 1H), 6.72-6.79 (m, 1H), 6.88-6.95 (m, 1H), 7.11 (td, J=7.71, 3.54 Hz, 1H).

Workup

  1. customAfter a fourth evacuation the flask was purged with H2
  2. filtrationThe reaction mixture was filtered through a pad of celite
  3. concentrationthe filtrate was concentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-b8f3b08a8c784565a44bc45440dec45c
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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