Cyanoacetamide → 4-Methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile

HRID 42483

反応式

HRID 42483 の反応式
[C:1]1([CH2:7][C:8](=O)[CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:14]([CH2:16][C:17]([NH2:19])=[O:18])#[N:15].N1CCCCC1>CCO.O>[CH3:11][C:10]1[NH:19][C:17](=[O:18])[C:16]([C:14]#[N:15])=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:9]=1.[CH3:11][C:10]1[CH:9]=[C:8]([CH2:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[NH:19][C:17](=[O:18])[C:16]=1[C:14]#[N:15]

参加物

7

反応物 3

HCID 7898CyanoacetamideHCID 8082PiperidineHCID 187232,4-Pentanedione, 1-phenyl-

生成物 2

HCID 674668016-Methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrileHCID 674670424-Methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile収率 103.4%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
75 °C

実験手順

1-Phenyl-2,4-pentanedione (18.32 g, 104 mmol) and cyanoacetamide (8.74 g, 104 mmol) were dissolved in EtOH (104 mL) and heated until homogenous (ca. 75° C.). Piperidine (8.86 g, 104 mmol) was added and the reaction mixture heated at reflux for 15-30 min. followed by cooling to room temperature, during which time precipitation occurred. The heterogenous contents were filtered to give a solid which was suspended in 200 mL water and stirred vigorously for 20 min. The heterogenous mixture was filtered to afford 6-methyl-2-oxo-4-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile and 4-methyl-2-oxo-6-(phenylmethyl)-1,2-dihydro-3-pyridinecarbonitrile (12.06 g, 52%). LCMS MH+=225.1

後処理

  1. temperaturethe reaction mixture heated
  2. temperatureat reflux for 15-30 min.
  3. temperatureby cooling to room temperature, during which time precipitation
  4. filtrationThe heterogenous contents were filtered
  5. customto give a solid which
  6. filtrationThe heterogenous mixture was filtered

出典と根拠

ORDレコード
ord-4a5291a1843c4cf5bf4c5ef412c25408
出典データセット
uspto-grants-2013_09
特許番号
US08536179B2

関連ノート

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