Malononitrile → HCID 69620617, 화합물

HRID 1826979노트

반응식

HRID 1826979 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 69620617HCID 69620617, 화합물수율 797.9%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-dd4f8202f2414f649aae71b17137c289
출처 데이터셋
uspto-grants-2006_05
특허 번호
US07053117B2

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