Ethyl cyanoacetate → HCID 69083032, compound

HRID 2206291Notes

Reaction equation

HRID 2206291 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].[F:12][C:13]1[CH:14]=[C:15]([CH:18]=[C:19]([F:22])[C:20]=1[F:21])[CH:16]=O.[C:23]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])#[N:24].N1CCCCC1>C(O)C.O>[CH2:29]([O:28][C:26]([C:25]1[CH:16]([C:15]2[CH:14]=[C:13]([F:12])[C:20]([F:21])=[C:19]([F:22])[CH:18]=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:23]=1[NH2:24])=[O:27])[CH3:30]

Participants

7

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 86632-NaphtholHCID 27769543,4,5-Trifluorobenzaldehyde

Product 1

HCID 69083032HCID 69083032, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

2-Naphthol (170 mg, 1.2 mmol), 3,4,5-trifluorobenzaldehyde (160 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, stirred for 1 h, solids were collected by filtration, washed with 60% aq ethanol and dried (346 mg, 0.86 mmol, 86%).

Workup

  1. temperatureThe reaction mixture was cooled down to room temperature
  2. stirringstirred for 1 h
  3. filtrationsolids were collected by filtration
  4. washwashed with 60% aq ethanol
  5. customdried (346 mg, 0.86 mmol, 86%)

Sources & evidence

ORD record
ord-f86b7bc147a44204a52e044d9849c771
Source dataset
uspto-grants-2016_06
Patent number
US09371333B2

Reaction notes

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