1-Naphthol → HCID 69291745, compound

HRID 2206273Notes

Reaction equation

HRID 2206273 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]([CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])#[N:26].N1CCCCC1>C(O)C.O>[CH2:31]([O:30][C:28]([C:27]1[CH:16]([C:15]2[CH:18]=[C:19]([O:23][CH3:24])[C:20]([O:21][CH3:22])=[C:13]([Br:12])[CH:14]=2)[C:2]2[C:1](=[C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]3=[CH:4][CH:3]=2)[O:11][C:25]=1[NH2:26])=[O:29])[CH3:32]

Participants

7

Reactant 4

HCID 70051-NaphtholHCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 813793-Bromo-4,5-dimethoxybenzaldehyde

Product 1

HCID 69291745HCID 69291745, 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 ethyl cyanoacetate (113 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 control till the reaction was complete. The reaction mixture was cooled down to room temperature, diluted with water to about 15 ml and stirred for 1 h at room temperature. The solids were collected by filtration, washed well with 60% aq. ethanol and dried under high vacuum (420 mg, 0.86 mmol, 86%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for 1 h at room temperature
  3. filtrationThe solids were collected by filtration
  4. washwashed well with 60% aq. ethanol
  5. customdried under high vacuum (420 mg, 0.86 mmol, 86%)

Sources & evidence

ORD record
ord-90385c89fcd44e04ad7a4931ea890138
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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