Hydrochloric Acid → (4-Aminophenyl)dimethylphosphine oxide hydrochloride

HRID 1745832Notes

Reaction equation

HRID 1745832 reaction equation
[CH3:1][P:2]([CH3:13])([C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=1)=[O:3].CCO.[ClH:17]>[Pd]>[ClH:17].[CH3:1][P:2]([CH3:13])([C:4]1[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=1)=[O:3]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 218979121-(Dimethyl-phosphinoyl)-4-nitro-benzene

Product 1

HCID 21897911(4-Aminophenyl)dimethylphosphine oxide hydrochloride

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

A suspension of 1-(Dimethyl-phosphinoyl)-4-nitro-benzene (2.04 g, 10.2 mmol) and 10% palladium on carbon (0.411 g) in 103 mL of absolute EtOH containing 1.15 mL (11.4 mmol) of conc. HCl was flushed with H2 and stirred at ambient temperature (H2 balloon) for 2 h. The reaction mixture was filtered through Celite, the Celite washed with EtOH, and the combined filtrates concentrated to provide the crude product. Recrystallization from boiling iPrOH (10 mL) provided, after several crops, 1.17 g of an off-white solid: 1H NMR (300 MHz, DMSO-d6) δ 7.61 (dd, J=11.1, 8.4 Hz, 2H), 7.04 (dd, J=8.4, 2.0 Hz, 2H), 1.64 (s, 3H), 1.60 (s, 3H). 31P NMR (121 MHz, DMSO-d6) δ 39.299.

Workup

  1. customwas flushed with H2
  2. filtrationThe reaction mixture was filtered through Celite
  3. washthe Celite washed with EtOH
  4. concentrationthe combined filtrates concentrated

Sources & evidence

ORD record
ord-62980339eda8411589318b087101cd41
Source dataset
uspto-grants-2006_03
Patent number
US07019139B2

Reaction notes

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