Toluene → ethyl 2,3-dihydro-2-oxo-1H-pyrrolo[1,2,3-de]quinoxaline-5-carboxylate

HRID 650050Notes

Reaction equation

HRID 650050 reaction equation
C([O:3][C:4]([CH2:6][N:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][C:14]=2[N+:16]([O-])=O)[CH:9]=[C:8]1[C:19]([O:21][CH2:22][CH3:23])=[O:20])=O)C.C1(C)C=CC=CC=1.C[O-].[Na+]>O1CCCC1.[C].[Pd]>[O:3]=[C:4]1[CH2:6][N:7]2[C:8]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[CH:9][C:10]3[C:15]2=[C:14]([CH:13]=[CH:12][CH:11]=3)[NH:16]1

Participants

6

Reactant 3

HCID 1140TolueneHCID 10942334Sodium MethoxideHCID 21714275ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate

Product 1

HCID 15432799ethyl 2,3-dihydro-2-oxo-1H-pyrrolo[1,2,3-de]quinoxaline-5-carboxylateYield 85.7%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 1-ethoxycarbonylmethyl-7-nitro-1H-indole-2-carboxylate (2.11 g, 6.59 mmol) was subjected to catalytic reduction in the presence of 10% palladium-carbon (0.20 g) in tetrahydrofuran (70 ml) at ordinary temperature and atmospheric pressure. After completion of the reaction, the catalyst was filtered off and the filtrate was concentrated under reduced pressure. Toluene (100 ml) and sodium methoxide (0.35 g, 6.48 mmol) were added to the residue, and the resulting mixture was heated under reflux for 2 hours. Then, the solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/8) to obtain ethyl 2,3-dihydro-2-oxo-1H-pyrrolo[1,2,3-de]quinoxaline-5-carboxylate (1.38 g).

Workup

  1. customAfter completion of the reaction
  2. filtrationthe catalyst was filtered off
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. temperaturethe resulting mixture was heated
  5. temperatureunder reflux for 2 hours
  6. distillationThen, the solvent was distilled off under reduced pressure
  7. customthe resulting residue was purified by a silica gel column chromatography (eluent: ethyl acetate/n-hexane=2/8)

Sources & evidence

ORD record
ord-403c4a5aa64647379ba11e47e6a3ce19
Source dataset
uspto-grants-2001_08
Patent number
US06271251B1

Reaction notes

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