Ethyl cyanoacetate → HCID 69507081, compound

HRID 1768419Notes

Reaction equation

HRID 1768419 reaction equation
COC1C=C(C=CC=1)C=O.C(CC(OCC)=O)#N.N1CCCCC1.[OH:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:27]=1[CH:28]=[CH:29][NH:30]2.[H-].[Na+].C([O:39][C:40](=O)[C:41]([C:51]#[N:52])=[CH:42][C:43]1[CH:48]=[CH:47][CH:46]=[C:45]([O:49][CH3:50])[CH:44]=1)C>C(O)C.C1(C)C=CC=CC=1>[C:51]([CH:41]1[C:42]([C:43]2[CH:48]=[CH:47][CH:46]=[C:45]([O:49][CH3:50])[CH:44]=2)=[C:34]2[C:26](=[C:27]3[CH:28]=[CH:29][N:30]=[C:31]3[CH:32]=[CH:33]2)[O:25][C:40]1=[O:39])#[N:52]

Participants

9

Reactant 6

HCID 7764Ethyl cyanoacetateHCID 8082PiperidineHCID 115693-MethoxybenzaldehydeHCID 24758Sodium hydrideHCID 754211H-indol-4-olHCID 3674973-(3-methoxyphenyl)-2-cyano-acrylic acid ethyl ester

Product 1

HCID 69507081HCID 69507081, compoundYield 0.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 1140TolueneSolvent2×

Procedure

To a solution of 3-methoxybenzaldehyde (2.0 g, 15.0 mmol) and ethyl cyanoacetate (1.56 mL, 15.0 mmol) in ethanol (10 mL) was added piperidine (0.73 ml, 7.5 mmol). The mixture was stirred at room temperature overnight. The solvent was evaporated and the crude oil was used for the next step. To a solution of 4-hydroxyindole (266.3 mg, 2 mmol) in toluene (5 mL) was added sodium hydride (100 mg, 2.5 mmol, 60%) and the mixture was stirred at room temperature for 0.5 h. To the mixture was added the 3-(3-methoxy-phenyl)-2-cyano-acrylic acid ethyl ester (462.5 mg, 2 mmol) dissolved in toluene (1 mL), then the mixture was refluxed for 2 h. The solvent was evaporated and the residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant, yielding 6 mg (0.9%) the title compound. 1H NMR (CDCl3): 8.67 (brs, 1H), 7.54-7.48 (m, 1H), 7.35-7.31 (m, 2H), 7.15-7.01 (m, 5H), 3.88 (s, 3H).

Workup

  1. customThe solvent was evaporated
  2. stirringthe mixture was stirred at room temperature for 0.5 h
  3. temperaturethe mixture was refluxed for 2 h
  4. customThe solvent was evaporated
  5. customthe residue was purified by chromatography on silica gel with ethyl acetate and hexane (1:2) as eluant

Sources & evidence

ORD record
ord-0d28738b75814e69ba81ae250129489e
Source dataset
uspto-grants-2007_06
Patent number
US07235674B2

Reaction notes

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