Malononitrile → HCID 69083139, compound

HRID 2206277Notes

Reaction equation

HRID 2206277 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH:4]=[CH:5][CH:6]=[C:7]2[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:12][C:7]2[C:6]([CH:17]([C:16]3[CH:19]=[C:20]([O:24][CH3:25])[C:21]([O:22][CH3:23])=[C:14]([Br:13])[CH:15]=3)[C:27]=1[C:28]#[N:29])=[CH:5][CH:4]=[C:3]1[C:2]([NH2:1])=[CH:11][CH:10]=[CH:9][C:8]=21

Participants

7

Reactant 4

HCID 8010MalononitrileHCID 9237DabcoHCID 657465-Amino-1-naphtholHCID 813793-Bromo-4,5-dimethoxybenzaldehyde

Product 1

HCID 69083139HCID 69083139, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

5-Amino-naphthol (700 mg, 4.4 mmol), 3-bromo-4,5-dimethoxy-benzaldehyde (1077 mg, 4.4 mmol) and malononitrile (295 mg, 4.4 mmol) were taken in 40 ml ethanol at room temperature, charged with DABCO (48.4 μl, 1.46 mmol) and then stirred at 80° C. under LC-MS control for 18 h. The reaction mixture was then cooled down to room temperature. The mixture was diluted with water to about 100 ml, stirred at room temperature for 1 h and the precipitates were separated by filtration. It was washed well with 50% aqueous ethanol and dried under vacuum (1.58 g, 3.5 mmol, 79.5%).

Workup

  1. temperatureThe reaction mixture was then cooled down to room temperature
  2. stirringstirred at room temperature for 1 h
  3. customthe precipitates were separated by filtration
  4. washIt was washed well with 50% aqueous ethanol
  5. customdried under vacuum (1.58 g, 3.5 mmol, 79.5%)

Sources & evidence

ORD record
ord-3837dc09dfdf444f8880784846205c12
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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