Malononitrile → HCID 69038031, compound

HRID 1826974Notes

Reaction equation

HRID 1826974 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:27]=[CH:28][CH:29]=[C:30]2[C:34]=1[NH:33][CH:32]=[CH:31]2>C(O)C>[NH2:17][C:16]1[O:25][CH:26]2[C:34]3[C:30](=[CH:29][CH:28]=[C:27]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])[CH:31]=[CH:32][N:33]=3

Participants

6

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 27376517-Hydroxyindole

Product 1

HCID 69038031HCID 69038031, compoundYield 13.1%

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 (4 mL) was added piperidine (0.05 mL, 0.5 mmol) and 7-hydroxyindole (133.2 mg, 1 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated and the residue was purified by chromatography on silica gel with EtOAc and hexane (1:2) as eluant, yielding 56 mg (13%) the title compound. 1H NMR (CDCl3): 8.39 (brs, 1H), 7.34–7.25 (m, 2H), 6.91 (d, J=2.1 Hz, 1H), 6.76 (d, J=2.1 Hz, 1H), 6.67 (d, J=8.1 Hz, 1H), 6.56 (q, J=2.1 Hz, 1H), 4.80 (s, 1H), 4.67 (brs, 2H), 3.84 (s, 3H), 3.83 (s, 3H).

Workup

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

Sources & evidence

ORD record
ord-686293a024854357a40fa60cd3fa8169
Source dataset
uspto-grants-2006_05
Patent number
US07053117B2

Reaction notes

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