Malononitrile → HCID 69084223, compound

HRID 2206276Notes

Reaction equation

HRID 2206276 reaction equation
[OH:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([OH:12])=[CH:4][CH:3]=1.[Br:13][C:14]1[CH:15]=[C:16]([CH:19]=[C:20]([O:24][CH3:25])[C:21]=1[O:22][CH3:23])[CH:17]=O.[C:26](#[N:30])[CH2:27][C:28]#[N:29].C1N2CCN(CC2)C1>C(O)C.O>[NH2:30][C:26]1[O:1][C:2]2[C:3]([CH:17]([C:16]3[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:14]([Br:13])[CH:15]=3)[C:27]=1[C:28]#[N:29])=[CH:4][C:5]([OH:12])=[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=21

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 9237DabcoHCID 113051,4-NaphthalenediolHCID 813793-Bromo-4,5-dimethoxybenzaldehyde

Product 1

HCID 69084223HCID 69084223, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1,4-Dihydroxy-naphthalene (704 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benz-aldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 μl, 1.46 mmol) and then refluxed with stirring under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50% aqueous ethanol and dried under vacuum (1.68 g, 3.7 mmol, 84%).

Workup

  1. temperaturerefluxed
  2. stirringstirred at room temperature for 1 h
  3. customthe precipitates were separated by filtration
  4. washIt was washed well with 50% aqueous ethanol
  5. customdried under vacuum (1.68 g, 3.7 mmol, 84%)

Sources & evidence

ORD record
ord-cbc858c109f240ad9c76bcd620b4822c
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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