Ethylene Glycol → N-(2-methoxyethyl)aniline

HRID 1883374Notes

Reaction equation

HRID 1883374 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:9][O:10][CH2:11][CH2:12][NH2:13].I[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[CH3:9][O:10][CH2:11][CH2:12][NH:13][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 80182-MethoxyethylamineHCID 11575IodobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 1581105N-(2-methoxyethyl)anilineYield 91.3%

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 3776IsopropanolSolventHCID 21226206Ethyl acetate hexaneSolvent

Procedure

The general procedure under argon or air was followed using copper(I) iodide (10 mg, 0.05 mmol or 2.0 mg, 0.01 mmol), K3PO4 (425 mg, 2.00 mmol), 2-methoxyethylamine (104 μL, 1.20 mmol), iodobenzene (112 μL, 1.00 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=10/1, Rƒ=0.2) afforded N-(2-methoxyethyl)aniline (138 mg, 91% isolated yield) as colorless liquid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Fancher, L. W.; Gless, R. D., Jr.; Wong, R. Y. Tetrahedron Lett. 1988, 29, 5095-5098.

Sources & evidence

ORD record
ord-3501fc2f48634894b246f73b1d7ad8c0
Source dataset
uspto-grants-2004_07
Patent number
US06759554B2

Reaction notes

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