Hydrochloric Acid → 6-Ethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonitrile

HRID 2095781노트

반응식

HRID 2095781 반응식
[C:1]([CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[O:5])#[N:2].CO/[CH:15]=[CH:16]/[C:17](=O)[CH2:18][CH3:19].N12CCN(CC1)CC2.Cl>COCCOCCO>[CH2:18]([C:17]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:4](=[O:5])[C:3]([C:1]#[N:2])=[CH:15][CH:16]=1)[CH3:19]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 9237DabcoHCID 69296Acetamide, 2-cyano-N-phenyl-HCID 10877086(1E)-1-methoxypent-1-en-3-one

생성물 1

HCID 669685986-Ethyl-2-oxo-1-phenyl-1,2-dihydropyridine-3-carbonitrile수율 27.3%

시약·촉매·용매 1

HCID 8134Diethylene Glycol Monomethyl Ether용매

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온도
120 °C

실험 절차

A solution of 2-cyano-N-phenylacetamide (1.08 g, 6.73 mmol), (1E)-1-methoxypent-1-en-3-one (1.0 g, 8.76 mmol) and 1,4-diazabicyclo[2.2.2]octane (755 mg, 6.73 mmol) in 2-(2-methoxyethoxy)ethanol (10 mL) was stirred with heating at 120° C. for 7 hr. 1N Hydrochloric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and filtered, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=2/1→4/1) to give the title compound (412 mg, 27%) as a pale-brown solid.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography (NH silica gel, ethyl acetate/hexane=2/1→4/1)

출처 및 근거

ORD 기록
ord-690c92b46f024cfb9171fb9fc2799830
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08445509B2

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