Ethyl Nicotinate → HCID 13958012, compound

HRID 580333Notes

Reaction equation

HRID 580333 reaction equation
[Na].[NH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH2:4][C:3]1=[O:11].[C:12](OCC)(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[N:15][CH:14]=1>C(O)C.O>[N:15]1[CH:16]=[CH:17][CH:18]=[C:13]([C:12]([CH:4]2[C:5]3[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=3)[NH:2][C:3]2=[O:11])=[O:19])[CH:14]=1

Participants

6

Reactant 3

HCID 69188Ethyl NicotinateHCID 321710OxindoleHCID 5360545Sodium

Product 1

HCID 13958012HCID 13958012, compoundYield 18.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of 2.1 g (0.090 mole) of sodium metal in 100 ml of ethanol, was added 10.0 g (0.075 mole) of 2-oxindole, followed by 13.6 g (0.090 mole) of ethyl nicotinate. The resulting slurry was heated under reflux for 3 hours and then the mixture was cooled and filtered. The residue was discarded, and the filtrate was evaporated in vacuo. The residue thus obtained was dissolved in ca. 150 ml of water, and the aqueous solution was washed with chloroform. To the aqueous solution was then added 5.8 ml of glacial acetic acid and the resulting mixture was cooled in an ice-bath. The solid was recovered by filtration and recrystallized from ethanol to give 3.3 g of the title compound as yellow needles, m.p. 169°-170° C.

Workup

  1. temperatureThe resulting slurry was heated
  2. temperatureunder reflux for 3 hours
  3. temperaturethe mixture was cooled
  4. filtrationfiltered
  5. customthe filtrate was evaporated in vacuo
  6. customThe residue thus obtained
  7. washthe aqueous solution was washed with chloroform
  8. additionTo the aqueous solution was then added 5.8 ml of glacial acetic acid
  9. temperaturethe resulting mixture was cooled in an ice-bath
  10. filtrationThe solid was recovered by filtration
  11. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-be5e86c7b65f4d94ab7673fac9f79931
Source dataset
uspto-grants-1988_06
Patent number
US04752609

Reaction notes

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