Ethyl cyanoacetate → HCID 69085878, compound

HRID 2206293Notes

Reaction equation

HRID 2206293 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[OH:11].[Br:12][C:13]1[C:14]([O:23][CH3:24])=[C:15]([O:21][CH3:22])[CH:16]=[C:17]([CH:20]=1)[CH:18]=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:18]([C:17]2[CH:16]=[C:15]([O:21][CH3:22])[C:14]([O:23][CH3:24])=[C:13]([Br:12])[CH:20]=2)[C:3]2[C:2](=[CH:1][C:10]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[CH:4]=2)[O:11][C:25]=1[NH2:26])=[O:29])[CH3:32]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 86632-NaphtholHCID 813793-Bromo-4,5-dimethoxybenzaldehyde

Product 1

HCID 69085878HCID 69085878, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Naphthol (170 mg, 1.2 mmol), 5-bromo-3,4-dimethoxy-benzaldehyde (245 mg, 1 mmol) and ethyl cyanoacetate (113 mg, 1 mmol) were taken in 5 ml ethanol at room temperature, charged with piperidine (50 μl) and then stirred at 80° C. for 18 h. Reaction was complete and clean. The reaction mixture was then cooled down to room temperature, diluted with water to 20 ml, solids were separated by filtration, washed with methanol and dried under high vacuum (360 mg, 74%).

Workup

  1. customReaction
  2. temperatureThe reaction mixture was then cooled down to room temperature
  3. customwere separated by filtration
  4. washwashed with methanol
  5. customdried under high vacuum (360 mg, 74%)

Sources & evidence

ORD record
ord-839e40e12fa1458b97e8e07ba3f269dc
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

Loading…