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

HRID 12553

Reaction equation

[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

Participants

Conditions

Temperature: 112 °C

Procedure

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.

Workup

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)

Sources & evidence

ORD record: ord-a2896fc6ab234e46af24b98823239a8b
Source dataset: uspto-grants-2010_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07728014B2

Linked notes

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