Ethyl cyanoacetate → HCID 57094953, compound

HRID 1957234Notes

Reaction equation

HRID 1957234 reaction equation
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]([CH:17]=O)=[C:9]1Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:20]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])#[N:21].[NH:28]1[CH2:33][CH2:32][O:31][CH2:30][CH2:29]1>CCO>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]2[CH:17]=[C:22]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:20]([N:28]3[CH2:33][CH2:32][O:31][CH2:30][CH2:29]3)=[N:21][C:9]1=2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 8083MorpholineHCID 105639332-Chloro-1-benzyl-1H-indole-3-carboxaldehyde

Product 1

HCID 57094953HCID 57094953, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a slurry of 1.35 g of 1-benzyl-2-chloroindole-3-carbaldehyde in 30 ml abs. EtOH was added 1.5 ml of ethyl cyanoacetate and 3.5 ml of morpholine, and the mixture was stirred at room temperature for 2 days. The mixture was then heated to reflux for 5 hours, cooled to room temperature and filtered to give (2b). Yield 1.6 g of (2b), m.p. 151°-152° C.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 5 hours
  3. temperaturecooled to room temperature
  4. filtrationfiltered

Sources & evidence

ORD record
ord-de950cb5330d40c7941ed734dabdb7d2
Source dataset
uspto-grants-1998_07
Patent number
US05783575

Reaction notes

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