Malononitrile → HCID 69620617、化合物

HRID 1826979ノート

反応式

HRID 1826979 の反応式
[CH:1]([C:3]1[CH:4]=[N:5][CH:6]=[C:7]([CH:10]=1)[C:8]#[N:9])=O.[C:11](#[N:15])[CH2:12][C:13]#[N:14].[OH:16][C:17]1[CH:25]=[CH:24][CH:23]=[C:22]2[C:18]=1[CH:19]=[CH:20][NH:21]2.N1CCCCC1>C(O)C>[NH2:14][C:13]1[O:16][CH:17]2[C:18]3[C:22](=[CH:23][CH:24]=[C:25]2[CH:1]([C:3]2[CH:4]=[N:5][CH:6]=[C:7]([C:8]#[N:9])[CH:10]=2)[C:12]=1[C:11]#[N:15])[N:21]=[CH:20][CH:19]=3

参加物

6

反応物 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 754211H-indol-4-olHCID 129198065-Formylpyridine-3-carbonitrile

生成物 1

HCID 69620617HCID 69620617、化合物収率 797.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a clear solution of 5-formyl-nicotinonitrile (0.0063 g, 0.048 mmol), ethanol (0.24 mL) and malononitrile (0.0031 g, 0.0048 mmol) was added 4-hydroxyindole (0.0064 g, 0.048 mmol) and piperidine (2.4 μL, 0.024 mmol). The resultant dark green solution was stirred at room temperature for 6 h, concentrated to a gray solid and extracted with EtOAc (30 mL). The organic layer was washed with water (5 mL), dried over MgSO4, filtered through sintered glass and concentrated to yield 0.012 g (80%) of a green solid. Purification by column chromatography (elution with EtOAC:hexanes, 1:2) yielded 0.006 g (40%) of the above compound as a white solid. 1H-NMR (Acetone-d6): 10.54 (s, 1H), 8.83 (t, J=2.20, 1.65 Hz, 2H), 8.09 (t, J=2.20, 1.92 Hz, 1H), 7.39 (t, J=2.75 Hz, 1H), 7.20 (dd, J=8.24, 0.82 Hz, 1H), 6.77 (dd, J=8.24 Hz, 1H), 6.58 (m, J=2.20, 1.92, 0.82 Hz, 1H), 6.42 (s, 2H), 5.09 (s, 1H).

後処理

  1. concentrationconcentrated to a gray solid
  2. extractionextracted with EtOAc (30 mL)
  3. washThe organic layer was washed with water (5 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered through sintered glass
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-dd4f8202f2414f649aae71b17137c289
出典データセット
uspto-grants-2006_05
特許番号
US07053117B2

反応ノート

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