Malononitrile → HCID 178487558, compound

HRID 2206281Notes

Reaction equation

HRID 2206281 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][C:2]=1[OH:12].[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:11][C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[N:1]=[C:2]([OH:12])[C:3]=2[CH:17]([C:16]2[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:14]([Br:13])[CH:15]=2)[C:27]=1[C:28]#[N:29]

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 9237DabcoHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 1785165532-hydroxy-1H-quinolin-4-one

Product 1

HCID 178487558HCID 178487558, compoundYield 87%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2,4-Quinolinediol (193 mg, 1.2 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (245 mg, 1 mmol) and malononitrile (66 mg, 1 mmol) were taken in 25 ml ethanol at room temperature, charged with DABCO (11 μl, 0.1 mmol) and then stirred at 80° C. under LC-MS control for 21 h whereby the reaction was complete. The reaction mixture was cooled down to room temperature, diluted with water to about 100 ml and stirred for over night at room temperature. The solids were collected by filtration, washed well with 50% aqueous ethanol and dried under high vacuum yielding 395 mg (0.87 mmol, 87%) of the pure title compound.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for over night at room temperature
  3. filtrationThe solids were collected by filtration
  4. washwashed well with 50% aqueous ethanol
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-08a2efcef6634161b2144e11a6cad676
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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