2-(Dimethylamino)ethanol → 5-(2-Dimethylamino-ethoxy)-2-nitro-phenylamine

HRID 1909008Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1909008
F[C:2]1[CH:3]=[C:4]([C:6]([N+:9]([O-:11])=[O:10])=[CH:7][CH:8]=1)[NH2:5].[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][OH:16].[OH-].[K+]>C1(C)C=CC=CC=1.O>[CH3:12][N:13]([CH3:17])[CH2:14][CH2:15][O:16][C:2]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[C:4]([NH2:5])[CH:3]=1

Komponenten

6

Edukt 3

HCID 79022-(Dimethylamino)ethanolHCID 14797Potassium HydroxideHCID 753995-Fluoro-2-nitroaniline

Produkt 1

HCID 203767455-(2-Dimethylamino-ethoxy)-2-nitro-phenylamineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3-Fluoro-6-nitroaniline (0.7 g, 4.48 mmol) and N,N-dimethylethanolamine (1.34 mL, 13.45 mmol) were dissolved in toluene (5 mL). This solution was cooled at 0° C. and finely ground KOH (1.258 g, 22.4 mmol) was added to the stirring mixture. The reaction mixture was stirred for 16 hours at room temperature, diluted with H2O (30 mL) and then extracted with CHCl3 (3×25 mL). The combined organics were dried (Na2SO4), filtered and the solvent was removed in vacuo. Purification by SiO2 chromatography (0% to 10% 2.0M NH3 in MeOH/dichloromethane) gave 5-(2-dimethylamino-ethoxy)-2-nitro-phenylamine as a dark oil (0.665 g, 90%). MS(ESI) m/z 226.0 (M+H)+

Aufarbeitung

  1. extractionextracted with CHCl3 (3×25 mL)
  2. dry with materialThe combined organics were dried (Na2SO4)
  3. filtrationfiltered
  4. customthe solvent was removed in vacuo
  5. customPurification by SiO2 chromatography (0% to 10% 2.0M NH3 in MeOH/dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-a30b3142357e4b5ab783a177a277fad8
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598217B2

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