Malononitrile → HCID 10203487, compound

HRID 1786532Notes

Reaction equation

HRID 1786532 reaction equation
[Br:1][C:2]1[C:3]([O:12][CH3:13])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=O.[C:14](#[N:18])[CH2:15][C:16]#[N:17].N1CCCCC1.[OH:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH:28]=[CH:29][CH:30]=[N:31]2>C(O)C>[NH2:17][C:16]1[O:25][C:26]2[C:27]3[CH:28]=[CH:29][CH:30]=[N:31][C:32]=3[CH:33]=[CH:34][C:35]=2[CH:7]([C:6]2[CH:5]=[C:4]([O:10][CH3:11])[C:3]([O:12][CH3:13])=[C:2]([Br:1])[CH:9]=2)[C:15]=1[C:14]#[N:18]

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082Piperidine2×HCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 135441757Quinolin-5-ol

Product 1

HCID 10203487HCID 10203487, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 5-bromoveratraldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) in ethanol (2 ml) was added piperidine (0.1 ml, 1 mmol). The mixture was stirred at room temperature for 15 min, then refluxed for 1 h, and cooled to room temperature. To the mixture was added piperidine (0.1 ml, 1 mmol) and 5-hydroxyquinoline (145 mg, 1 mmol). The mixture was refluxed for 1 h, and the solvent was evaporated. The residue was purified by chromatography on silica gel (EtOAc/hexane, 1:2), yielding the title compound (50 mg, 11%). 1H NMR (CDCl3): 8.95 (s, 1H), 8.50 (d, J=9.0, 1H), 7.82 (d, J=9.0, 1H), 7.50 (brs, 1H), 7.30 (s, 1H), 6.92 (s, 1H), 6.76 (s, 1H), 4.82 (brs, 3H), 3.84 (s, 6H).

Workup

  1. temperaturerefluxed for 1 h
  2. temperaturecooled to room temperature
  3. temperatureThe mixture was refluxed for 1 h
  4. customthe solvent was evaporated
  5. customThe residue was purified by chromatography on silica gel (EtOAc/hexane, 1:2)

Sources & evidence

ORD record
ord-d9a3a53e3d734a35b41bdca07ea9ab63
Source dataset
uspto-grants-2009_03
Patent number
US07507762B2

Reaction notes

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