Malononitrile → HCID 69080936, compound

HRID 2206290Notes

Reaction equation

HRID 2206290 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[CH2:12]([O:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][C:19]([CH:20]=O)=[CH:18][C:17]=1[Br:26])[CH:13]=[CH2:14].[C:27](#[N:31])[CH2:28][C:29]#[N:30].N1CCCCC1>C(O)C.O>[CH2:12]([O:15][C:16]1[C:23]([O:24][CH3:25])=[CH:22][C:19]([CH:20]2[C:3]3[C:2](=[CH:1][C:10]4[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=4[CH:4]=3)[O:11][C:27]([NH2:31])=[C:28]2[C:29]#[N:30])=[CH:18][C:17]=1[Br:26])[CH:13]=[CH2:14]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 8082PiperidineHCID 86632-NaphtholHCID 21681633-Bromo-5-methoxy-4-(2-propen-1-yloxy)benzaldehyde

Product 1

HCID 69080936HCID 69080936, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Naphthol (170 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 (235 mg, 0.51 mmol, 51%).

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 (235 mg, 0.51 mmol, 51%)

Sources & evidence

ORD record
ord-3fffd1d8ea4e45bfb240fae427d09889
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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