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

HRID 2095781ノート

反応式

HRID 2095781 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8134Diethylene Glycol Monomethyl Ether溶媒

反応条件

温度
120 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-690c92b46f024cfb9171fb9fc2799830
出典データセット
uspto-grants-2013_05
特許番号
US08445509B2

反応ノート

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