Ethyl 1-oxo-2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate → HCID 19696125, compound

HRID 863682Notes

Reaction equation

HRID 863682 reaction equation
O=[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]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]>[Ni].C(O)C.O>[CH2:2]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]1[C:14]([O:16][CH2:17][CH3:18])=[O:15]

Participants

5

Reactant 1

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

Product 1

HCID 19696125HCID 19696125, compoundYield 13.3%

Reagents, catalysts & solvents 3

HCID 935NickelCatalyst2×HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

6 spoon spatula measures of Raney nickel were added to a solution of 5.08 g of ethyl 2,3-dihydro-1-oxo-1H-pyrrolo[1,2-a]indole-2-carboxylate in 180 ml of ethanol and 90 ml of water. The mixture was heated to reflux for 10 hours. Then, an additional 3 spoon spatula measures of Raney nickel were added. Heating was continued for 5.5 hours, whereupon the mixture was cooled and filtered. The filter residue was washed with ethyl acetate and dichloromethane. The combined filtrate and washings were evaporated and the residue was purified by chromatography on silica gel with diethyl ether/petroleum ether (1:2). Crystallization from methanol gave 635 mg of ethyl 2,3-dihydro-1H-pyrrolo[1,2-a]indole-2-carboxylate of melting point 55°-57° C.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 10 hours
  3. temperatureHeating
  4. temperaturewas cooled
  5. filtrationfiltered
  6. washThe filter residue was washed with ethyl acetate and dichloromethane
  7. customThe combined filtrate and washings were evaporated
  8. customthe residue was purified by chromatography on silica gel with diethyl ether/petroleum ether (1:2)
  9. customCrystallization from methanol

Sources & evidence

ORD record
ord-9aa3e2ff649d48418bee6db9abced18f
Source dataset
uspto-grants-1998_02
Patent number
US05721245

Reaction notes

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