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
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 1H NMR (400 MHz, DMSO-d6) δ 7.21-7.31 (m, 10H), 6.06 (s, 2H), 3.89 (s, 2H), 3.79 (s, 2H), 2.24 (s, 3H), 2.15 (s, 3H).
後処理
- temperaturethe reaction mixture heated
- temperatureat reflux for 15-30 min.
- temperatureby cooling to room temperature, during which time precipitation
- filtrationThe heterogenous contents were filtered
- customto give a solid which
- filtrationThe heterogenous mixture was filtered
出典と根拠
- ORDレコード
- ord-0f13a2e6dc0a4f008c61b5be5423639c
- 出典データセット
- uspto-grants-2014_09
- 特許番号
- US08846935B2
関連ノート
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