1-Naphthol → HCID 9803111, compound

HRID 2206268Notes

Reaction equation

HRID 2206268 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[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].N1CCCCC1>C(O)C.O>[NH2:29][C:25]1[O:11][C:1]2[C:2]([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:3][CH:4]=[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=21

Participants

7

Reactant 4

HCID 70051-NaphtholHCID 8010MalononitrileHCID 8082PiperidineHCID 813793-Bromo-4,5-dimethoxybenzaldehyde

Product 1

HCID 9803111HCID 9803111, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-Naphthol (170 mg, 1.2 mmol), 3-bromo-4,5-dimethoxybenzaldehyde (245 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 (Liquid chromatography-mass spectrometry) control till the reaction was complete. The reaction mixture was cooled down to room temperature and diluted with water to about 15 ml drop wise addition. The mixture was stirred at room temperature for about 1 h. Thus formed precipitates were collected by filtration, washed well with 60% aqueous ethanol and dried under high vacuum to get 394 mg (0.90 mmol, 90%) of the pure solids of the title compound.

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringThe mixture was stirred at room temperature for about 1 h
  3. customThus formed
  4. customprecipitates
  5. filtrationwere collected by filtration
  6. washwashed well with 60% aqueous ethanol
  7. customdried under high vacuum

Sources & evidence

ORD record
ord-094156185a2a4535a0adf9d2091675a8
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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