Ethyl Alpha-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate → Ethyl 5,6-dichloro-1H-indole-2-carboxylate

HRID 1602997Notes

Reaction equation

HRID 1602997 reaction equation
O=[C:2]([CH2:8][C:9]1[CH:14]=[C:13]([Cl:15])[C:12]([Cl:16])=[CH:11][C:10]=1[N+:17]([O-])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4]>CCO.C(O)(=O)C.[Fe]>[Cl:15][C:13]1[CH:14]=[C:9]2[C:10](=[CH:11][C:12]=1[Cl:16])[NH:17][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:8]2

Participants

5

Reactant 1

HCID 10733409Ethyl Alpha-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate

Product 1

HCID 10801165Ethyl 5,6-dichloro-1H-indole-2-carboxylateYield 92%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

A mixture of ethyl α-oxo-3-(2-nitro-4,5-dichlorophenyl)propanoate (100 g, 327 mmol) and iron powder (160 g) in EtOH (625 ml) and acetic acid (625 ml) was refluxed for two hours. After cooling, the resulting mixture was evaporated under vacuum and the solid residue was dissolved in THF (1000 ml) and chromatographed on Florisil (500 g) eluting with THF (5000 ml). Evaporation of the collected fractions gave pure title compound (77.5 g, 301 mmol, yield 92.0%) as a light brown powder, m.p. 215°-218° C.

Workup

  1. temperaturewas refluxed for two hours
  2. temperatureAfter cooling
  3. customthe resulting mixture was evaporated under vacuum
  4. dissolutionthe solid residue was dissolved in THF (1000 ml)
  5. customchromatographed on Florisil (500 g)
  6. washeluting with THF (5000 ml)
  7. customEvaporation of the collected fractions

Sources & evidence

ORD record
ord-b2ebdb1b041b4143aa357d84939f00da
Source dataset
uspto-grants-1999_11
Patent number
US05985905

Reaction notes

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