Malononitrile → HCID 178487559, compound

HRID 2206279Notes

Reaction equation

HRID 2206279 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])C=[CH:4][N:3]=1.[Br:9][C:10]1[CH:11]=[C:12]([CH:15]=[C:16]([O:20][CH3:21])[C:17]=1[O:18][CH3:19])[CH:13]=O.[C:22](#[N:26])[CH2:23][C:24]#[N:25].C1N2CC[N:29](CC2)C1>C(O)C.O>[NH2:25][C:24]1[O:1][C:2]2[N:3]=[CH:4][N:29]=[C:6]([OH:8])[C:7]=2[CH:13]([C:12]2[CH:15]=[C:16]([O:20][CH3:21])[C:17]([O:18][CH3:19])=[C:10]([Br:9])[CH:11]=2)[C:23]=1[C:22]#[N:26]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 9237DabcoHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 178516518HCID 178516518, compound

Product 1

HCID 178487559HCID 178487559, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Dihydroxypyridine (488 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 2 ml ethanol at room temperature, charged with DABCO (48.4 μl, 1.46 mmol, 30% mol) and then stirred at 80° C. 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 (1.47 g, 3.64 mmol, 82.7%).

Workup

  1. temperatureThe reaction mixture was then cooled down to room temperature
  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 (1.47 g, 3.64 mmol, 82.7%)

Sources & evidence

ORD record
ord-b746817f165644dab84de0f49ca5c5f6
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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