Malononitrile → HCID 178487554, compound

HRID 2206283Notes

Reaction equation

HRID 2206283 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[OH:11])[CH:4]=[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:9]2[C:10]3[C:5](=[CH:4][CH:3]=[C:2]([OH:12])[N:1]=3)[CH:6]=[CH:7][C:8]=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 178515617HCID 178515617, compound

Product 1

HCID 178487554HCID 178487554, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

2,8-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 (33 μl, 0.3 mmol) and then stirred at 90° C. under LC-MS control for 3 days. The reaction mixture was then cooled down to room temperature, diluted with water to about 100 ml and extracted with ethyl acetate (2×50 ml). The organic solution was washed with 5% aqueous sodium bicarbonate solution (2×50 ml) and then dried over magnesium sulfate, solvent was evaporated under vacuum at 40 C and dried (18 mg, 0.04 mmol, 4%).

Workup

  1. temperatureThe reaction mixture was then cooled down to room temperature
  2. extractionextracted with ethyl acetate (2×50 ml)
  3. washThe organic solution was washed with 5% aqueous sodium bicarbonate solution (2×50 ml)
  4. dry with materialdried over magnesium sulfate, solvent
  5. customwas evaporated under vacuum at 40 C
  6. customdried (18 mg, 0.04 mmol, 4%)

Sources & evidence

ORD record
ord-baf1263b63f9416a830fea80fc004d46
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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