Sulfuric Acid → 4-chloro-5-fluoro-1H-indole-2,3-dione

HRID 245136

반응식

HRID 245136 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10](=[O:14])[CH:11]=NO)[CH:5]=[CH:6][C:7]=1[F:8].[OH:15]S(O)(=O)=O>>[Cl:1][C:2]1[CH:3]=[C:4]2[C:5]([C:11](=[O:15])[C:10](=[O:14])[NH:9]2)=[CH:6][C:7]=1[F:8].[Cl:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[C:4]2[C:3]=1[C:11](=[O:15])[C:10](=[O:14])[NH:9]2

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 73843641N-(3-chloro-4-fluorophenyl)-2-(hydroxyimino)ethanamide

생성물 2

HCID 149861234-chloro-5-fluoro-1H-indole-2,3-dioneHCID 217955255-Fluoro-6-chloroisatin

반응 조건

온도
90 °C

실험 절차

To concentrated H2SO4 (100 ml) at 65° C. was added N-(3-chloro-4-fluorophenyl)-2-(hydroxyimino)ethanamide (19.45 g, 90 mmol) portionwise. The mixture was heated at 90° C. for 1.5 h. The mixture was cooled to room temperature, poured onto ice, and stirred for 10 min. The solid was collected by filtration, washed with water, and air dried to afford 6-chloro-5-fluoro-1H-indole-2,3-dione and 4-chloro-5-fluoro-1H-indole-2,3-dione as a mixture of regioisomers (15.5 g, 86% yield). This material was used without further purification.

후처리

  1. temperatureThe mixture was cooled to room temperature
  2. additionpoured onto ice
  3. filtrationThe solid was collected by filtration
  4. washwashed with water, and air
  5. customdried

출처 및 근거

ORD 기록
ord-e69cad0a06c648e38b823054c26ef33f
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08658636B2

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