Ammonium Chloride → 3-(Dimethylphosphoryl)aniline

HRID 409957

Reaktionsgleichung

Reaktionsgleichung von HRID 409957
[CH3:1][P:2]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([N+:11]([O-])=O)[CH:6]=1)([CH3:4])=[O:3].[Cl-].[NH4+]>CO.O.[Fe]>[CH3:4][P:2]([C:5]1[CH:6]=[C:7]([CH:8]=[CH:9][CH:10]=1)[NH2:11])([CH3:1])=[O:3]

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 1902781-Dimethylphosphoryl-3-nitrobenzene

Produkt 1

HCID 582077813-(Dimethylphosphoryl)anilineAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a solution of compound 286 (1.5 g, 7.5 mmol) in methanol (62 ml) and water (12 ml) under nitrogen at room temperature was added ammonium chloride (0.604 g, 11.3 mmol) and iron (1.68 g, 30.1 mmol). The resulting mixture was heated to reflux for 30 min then filtered through celite. The celite pad was rinsed with methanol. The filtrate and washings were combined and concentrated and the residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column) to afford compound 287 as a yellow solid (1.27 g, 7.51 mmol, quantitative). MS (m/z): 170.1 (M+H).

Aufarbeitung

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 30 min
  3. filtrationthen filtered through celite
  4. washThe celite pad was rinsed with methanol
  5. concentrationconcentrated
  6. customthe residue was purified via Biotage (linear gradient 0-20%, methanol/dichloromethane; 25M column)

Quellen und Nachweise

ORD-Eintrag
ord-28bb42a3a65344309b891ef14b6857dd
Quelldatensatz
uspto-grants-2014_06
Patentnummer
US08759522B2

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