Malononitrile → HCID 69620617, compound

HRID 1826979Notes

Reaction equation

HRID 1826979 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

HCID 69620617HCID 69620617, compoundYield 797.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-dd4f8202f2414f649aae71b17137c289
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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