Ethylene Glycol → N-benzyl-3-nitroaniline

HRID 1883362노트

반응식

HRID 1883362 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

HCID 682324N-benzyl-3-nitroaniline수율 72%

시약·촉매·용매 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 3776Isopropanol용매HCID 21226206Ethyl acetate hexane용매

실험 절차

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, Rƒ=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.

출처 및 근거

ORD 기록
ord-b5ef14a53f8a477fb00b57356f88fa91
출처 데이터셋
uspto-grants-2004_07
특허 번호
US06759554B2

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