Malononitrile → HCID 10203487, compound

HRID 2206282Notes

Reaction equation

HRID 2206282 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[N:7]2.[Br:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([O:23][CH3:24])[C:20]=1[O:21][CH3:22])[CH:16]=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[C:11]([CH:16]([C:15]3[CH:18]=[C:19]([O:23][CH3:24])[C:20]([O:21][CH3:22])=[C:13]([Br:12])[CH:14]=3)[C:26]=1[C:27]#[N:28])=[CH:10][CH:9]=[C:8]1[C:3]=2[CH:4]=[CH:5][CH:6]=[N:7]1

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 9237DabcoHCID 813793-Bromo-4,5-dimethoxybenzaldehydeHCID 135441757Quinolin-5-ol

Product 1

HCID 10203487HCID 10203487, compoundYield 36%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Hydroxyquinoline (174 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. The reaction mixture was cooled down to the room temperature, diluted with water to about 100 ml and stirred for over night. The solids were collected by filtration, washed with well 1:1 mixture of ethanol/water and dried under high vacuum yielding 134 mg (0.36 mmol, 36%) of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled down to the room temperature
  2. stirringstirred for over night
  3. filtrationThe solids were collected by filtration
  4. washwashed with well 1:1 mixture of ethanol/water
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-e8d3022772944e9fa4b4849d043e4179
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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