Ethylene Glycol → N-benzyl-3-nitroaniline

HRID 1243011Notes

Reaction equation

HRID 1243011 reaction equation
[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:9]([NH2:16])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.I[C:18]1[CH:19]=[C:20]([N+:24]([O-:26])=[O:25])[CH:21]=[CH:22][CH:23]=1.C(O)CO>[Cu]I.CCCCCC.C(OCC)(=O)C.CC(O)C>[N+:24]([C:20]1[CH:19]=[C:18]([NH:16][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:23]=[CH:22][CH:21]=1)([O-:26])=[O:25]

Participants

8

Reactant 4

HCID 174Ethylene GlycolHCID 7504BenzylamineHCID 125741-Iodo-3-nitrobenzeneHCID 62657Potassium Phosphate, Tribasic

Product 1

HCID 682324N-benzyl-3-nitroanilineYield 72%

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 was followed using copper(I) iodide (10 mg, 0.05 mmol), K3PO4 (425 mg, 2.00 mmol), benzylamine (109 μL, 1.00 mmol), 3-iodonitrobenzene (349 mg, 1.40 mmol), ethylene glycol (111 μL, 2.00 mmol) and 2-propanol (1.0 mL). Column chromatography using a solvent mixture (hexane/ethyl acetate=5/1, Rf=0.4) afforded N-(3-nitrophenyl)benzylamine (164 mg, 72% isolated yield) as orange solid. The spectral data (1H NMR) matched with the literature references and GC analysis indicated >95% purity. See Leardini, R.; Nanni, D.; Tundo, A.; Zanardi, G.; Ruggieri, F. J. Org. Chem. 1992, 57, 1842–1848.

Sources & evidence

ORD record
ord-aa34540dd6dd4f15816800c8ecbcb59d
Source dataset
uspto-grants-2006_10
Patent number
US07115784B2

Reaction notes

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