Ethyl Acrylate → Ethyl 1-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate

HRID 22284Notes

Reaction equation

HRID 22284 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[C:2]1[C:10]([O:12]CC)=O.[H-].[Na+].[C:17]([O:21][CH2:22][CH3:23])(=[O:20])[CH:18]=[CH2:19]>C1(C)C=CC=CC=1>[O:12]=[C:10]1[C:2]2=[CH:3][C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:9]=3[N:1]2[CH2:19][CH:18]1[C:17]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 8821Ethyl Acrylate2×HCID 24758Sodium hydride2×HCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 12582025Ethyl 1-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of ethyl indole-2-carboxylate (5.67 g, 30 mmol) in 400 ml of toluene under N was treated with sodium hydride (1.44 g, 36 mmol). Ethyl acrylate (3.6 ml, 33 mol) was added and the mixture was heated at reflux. Additional portions of ethyl acrylate (6 mmol) and sodium hydride (16 mmol) were added after 3 hr. After a total time of 6 hr, t.l.c. indicated that all starting material are consumed. The mixture was quenched with ethanol and treated with water, dilute HCl, and methylene chloride. The organic phase was washed with brine, dried over sodium sulfate, filtered, and concentrated to give 2,3-dihydro-1-oxo-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole, which was used directly in the next step.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux
  3. customAfter a total time of 6 hr, t.l.c
  4. customare consumed
  5. customThe mixture was quenched with ethanol
  6. additiontreated with water, dilute HCl, and methylene chloride
  7. washThe organic phase was washed with brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-49360bbee81a41c1b03e15e13a9f02f7
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Reaction notes

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