Malononitrile → HCID 3260543, compound

HRID 2206301Notes

Reaction equation

HRID 2206301 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([OH:10])=[CH:4][C:3]=2[O:2]1.[CH2:11]([O:14][C:15]1[C:22]([O:23][CH3:24])=[CH:21][C:18]([CH:19]=O)=[CH:17][C:16]=1[Br:25])[CH:12]=[CH2:13].[C:26](#[N:30])[CH2:27][C:28]#[N:29].N1CCCCC1>C(O)C.O>[CH2:11]([O:14][C:15]1[C:22]([O:23][CH3:24])=[CH:21][C:18]([CH:19]2[C:6]3[CH:7]=[C:8]4[O:9][CH2:1][O:2][C:3]4=[CH:4][C:5]=3[O:10][C:26]([NH2:30])=[C:27]2[C:28]#[N:29])=[CH:17][C:16]=1[Br:25])[CH:12]=[CH2:13]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 68289SesamolHCID 21681633-Bromo-5-methoxy-4-(2-propen-1-yloxy)benzaldehyde

Product 1

HCID 3260543HCID 3260543, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

3,4-Methylenedioxyphenol (166 mg, 1.2 mmol), 4-allyloxy-3-bromo-5-methoxy-benzaldehyde (271 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) were taken in 7 ml ethanol at room temperature, charged with piperidine (50 μL) and then stirred at 80° C. under LC-MS control till the reaction was complete. The reaction mixture was cooled down to room temperature, diluted with 10 ml water, stirred for 2 h at room temperature, solids were collected by filtration, washed with 1:1 mixture of ethanol/water and dried (200 mg, 0.44 mmol, 44%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for 2 h at room temperature
  3. filtrationsolids were collected by filtration
  4. washwashed with 1:1 mixture of ethanol/water
  5. customdried (200 mg, 0.44 mmol, 44%)

Sources & evidence

ORD record
ord-51cd70c852f74467ab2482d14ea55c12
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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