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

HRID 1602997ノート

反応式

HRID 1602997 の反応式
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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 176Acetic Acid溶媒HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-b2ebdb1b041b4143aa357d84939f00da
出典データセット
uspto-grants-1999_11
特許番号
US05985905

反応ノート

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