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

HRID 22285Notes

Reaction equation

HRID 22285 reaction equation
[O:1]=[C:2]1[C:6]2=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]2[CH2:4][CH:3]1C(OCC)=O>C(O)(=O)C.O>[O:1]=[C:2]1[C:6]2=[CH:7][C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=3[N:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 1

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

Product 1

HCID 105590922,3-Dihydro-1H-pyrrolo[1,2-a]indol-1-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 2,3-dihydro-1-oxo-2-ethoxycarbonyl-1H-pyrrolo[1,2-a]indole in 400 mL of acetic acid and 25 mL of water was heated at reflux under N2 for 16 hr. The resulting solution was cooled and concentrated to dryness. The residue was treated with water and methylene chloride. The organic layer was washed with NaHCO3, brine, dried and concentrated to give solid which was purified by column chromatography to give the title compound. HNMR (CDCl3)δ 2.17 (t, 2H), 4.38 (t, 2H), 6.95 (s, 1H), 7.06-7.2 (m, 1H), 7.2-7.4 (m, 2H), 7.7 (d, 1H) ppm.

Workup

  1. temperatureat reflux under N2 for 16 hr
  2. temperatureThe resulting solution was cooled
  3. concentrationconcentrated to dryness
  4. additionThe residue was treated with water and methylene chloride
  5. washThe organic layer was washed with NaHCO3, brine
  6. customdried
  7. concentrationconcentrated
  8. customto give solid which
  9. customwas purified by column chromatography

Sources & evidence

ORD record
ord-4935e285242f4fa0aa7aa811a5f5c13f
Source dataset
uspto-grants-1995_06
Patent number
US05428043

Reaction notes

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