1,10-Phenanthroline → 4-(2-Methoxyethoxy)aniline

HRID 657219Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 657219
I[C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH3:9][O:10][CH2:11][CH2:12][OH:13].C(=O)([O-])[O-].[Cs+].[Cs+].N1C2C(=CC=C3C=2N=CC=C3)C=CC=1>C1(C)C=CC=CC=1.[Cu](I)I>[CH3:9][O:10][CH2:11][CH2:12][O:13][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1

Komponenten

7

Edukt 4

HCID 13181,10-PhenanthrolineHCID 80192-MethoxyethanolHCID 10796Cesium carbonateHCID 108934-Iodoaniline

Produkt 1

HCID 38798854-(2-Methoxyethoxy)anilineAusbeute 5,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 83717Copper iodideKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 4-iodoaniline (219 mg, 1.0 mmol), 2-methoxyethanol (152 mg, 2.0 mmol), copper iodide (19.0 mg, 0.1 mmol), cesium carbonate (554 mg, 1.7 mmol) and 1,10-phenanthroline (36.0 mg, 0.2 mmol) was stirred in toluene (0.5 mL) at 110° C. overnight. The reaction was then cooled to RT and filtered through silica gel and washed with diethyl ether. The ether was removed in vacuo to obtain a crude solid. Purification by prep tlc (1:9 MeOH/DCM) afforded the title compound as a solid (8.9 mg, 5.3%). 1H NMR (300 MHz, CDCl3) δ 6.82-6.72 (m, 4H), 4.06 (t, 2H), 3.72 (t, 2H), 3.45 (s, 3H).

Aufarbeitung

  1. filtrationfiltered through silica gel
  2. washwashed with diethyl ether
  3. customThe ether was removed in vacuo
  4. customto obtain a crude solid
  5. customPurification by prep tlc (1:9 MeOH/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-94cdd682e822425a8201c95c172090f5
Quelldatensatz
uspto-grants-2011_12
Patentnummer
US08071768B2

Notizen zur Reaktion

Wird geladen…