Malononitrile → HCID 69085959, compound

HRID 2206296Notes

Reaction equation

HRID 2206296 reaction equation
[OH:1][C:2]1[N:3]=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[Br:12][C:13]1[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([CH:20]=1)[CH:18]=O.[C:25](#[N:29])[CH2:26][C:27]#[N:28].C1N2CCN(CC2)C1>C(O)C.O>[NH2:29][C:25]1[O:1][C:2]2[N:3]=[CH:4][C:5]3[C:10]([C:11]=2[CH:18]([C:17]2[CH:16]=[C:15]([O:21][CH3:22])[C:14]([O:23][CH3:24])=[C:13]([Br:12])[CH:20]=2)[C:26]=1[C:27]#[N:28])=[CH:9][CH:8]=[CH:7][CH:6]=3

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 9237DabcoHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 178515325HCID 178515325, compound

Product 1

HCID 69085959HCID 69085959, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3-Hydroxyisoquinoline (638 mg, 4.4 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde (1.077 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 stirred at 80° C. under LC-MS control for 24 h. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and the precipitates were collected by filtration, washed well with 50% aqueous ethanol and dried under vacuum to yield the title compound (1.35 g, 3.08 mmol, 70%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. filtrationthe precipitates were collected by filtration
  3. washwashed well with 50% aqueous ethanol
  4. customdried under vacuum

Sources & evidence

ORD record
ord-75be51b1d5704b73bc7a19380f7d762b
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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