Hydrochloric Acid → (4-Aminophenyl)dimethylphosphine oxide hydrochloride

HRID 50625

Reaktionsgleichung

Reaktionsgleichung von HRID 50625
[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]

Komponenten

5

Edukt 3

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

Produkt 1

HCID 21897911(4-Aminophenyl)dimethylphosphine oxide hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 23938PalladiumKatalysator

Versuchsvorschrift

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) δ7.61 (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) δ39.299.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-865a1e35446f47a3923a1d7b1b815098
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06713462B2

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