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

HRID 12553

반응식

HRID 12553 반응식
[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

참가 물질

5

반응물 3

HCID 8070N,N'-DimethylethylenediamineHCID 14789610Ethyl 5,6-diphenylpyridine-2-carboxylate2회HCID 16682925Trimethylaluminum

생성물 1

HCID 593388261-(5,6-Diphenyl-pyridin-2-yl)-ethanone

시약·촉매·용매 1

HCID 1140Toluene용매

반응 조건

온도
112 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-a2896fc6ab234e46af24b98823239a8b
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07728014B2

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