N,N'-Dimethylethylenediamine → 1-(5,6-Diphenyl-pyridin-2-yl)-ethanone

HRID 12553

Reaktionsgleichung

[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19]([O:21]CC)=O)=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:24]NCCNC.C[Al](C)C>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[CH:9][C:10]([C:19](=[O:21])[CH3:24])=[N:11][C:12]=2[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

Reaktionsbedingungen

Temperatur: 112 °C

Versuchsvorschrift

General Procedure O. To a solution of ethyl 5,6-diphenylpyridine-2-carboxylate (Compound 21, 246 mg, 0.81 mmol) in toluene (5 ml) was added N,N′-dimethylethylenediamine (DMEDA, 78.7 mg, 0.89 mmol) and trimethylaluminum (1.2 ml, 2.44 mmol, 2 M in toluene) dropwise under argon at room temperature. After the mixture was refluxed at 112° C. for 2.5 hours, it was quenched with water, and the products were extracted with ethyl acetate. The combined organic layers were washed with brine, and dried over Na2SO4. The filtered solvents were concentrated in vacuo, and the residue was purified by silica gel chromatography (15% ethyl acetate in hexane) to give title compound as a yellow solid.

Aufarbeitung

customit was quenched with water
extractionthe products were extracted with ethyl acetate
washThe combined organic layers were washed with brine
dry with materialdried over Na2SO4
concentrationThe filtered solvents were concentrated in vacuo
customthe residue was purified by silica gel chromatography (15% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag: ord-a2896fc6ab234e46af24b98823239a8b
Quelldatensatz: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07728014B2

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