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

HRID 1602997노트

반응식

HRID 1602997 반응식
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

참가 물질

5

반응물 1

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 176Acetic Acid용매HCID 702Ethanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b2ebdb1b041b4143aa357d84939f00da
출처 데이터셋
uspto-grants-1999_11
특허 번호
US05985905

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