Malononitrile → HCID 9943960, compound

HRID 1826973Notes

Reaction equation

HRID 1826973 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=O)[CH:6]=[N:7][CH:8]=1.[C:11](#[N:15])[CH2:12][C:13]#[N:14].N1CCCCC1.[NH2:22][C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1>C(O)C>[NH2:14][C:13]1[O:29][C:25]2[C:26]([CH:9]([C:5]3[CH:6]=[N:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=3)[C:12]=1[C:11]#[N:15])=[CH:27][CH:28]=[C:23]([NH2:22])[CH:24]=2

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 115683-AminophenolHCID 109755495-Methoxy-3-pyridinecarboxaldehyde

Product 1

HCID 9943960HCID 9943960, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 5-methoxypyridine-3-carboxaldehyde (69.2 mg, 0.5 mmol) and malononitrile (34 mg, 0.5 mmol) in ethanol (2.5 mL) was added piperidine (0.1 mL, 1 mmol) and 3-aminophenol (60 mg, 0.55 mmol). The mixture was stirred for 2 h under argon at room temperature. The solvent was evaporated and the residue was purified by chromatography on silica gel with hexane: EtOAc (4:1˜1:1) as eluant, yielding 44 mg of (31%) the title compound. 1H NMR (CD3OD): 8.02 (s, 1H), 7.88 (s, 1H), 6.93 (s, 1H), 6.75 (s, 1H), 6.51 (d, J=8.4 Hz, 1H), 6.18 (d, J=8.4 Hz, 1H), 6.09 (s, 1H), 5.15 (br, 1H), 4.49 (s, 1H), 3.66 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by chromatography on silica gel with hexane: EtOAc (4:1˜1:1) as eluant

Sources & evidence

ORD record
ord-292b8929e4004e61ad1da77488cbaac5
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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