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

HRID 245136

反応式

HRID 245136 の反応式
[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

参加物

4

反応物 2

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

生成物 2

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

反応条件

温度
90 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e69cad0a06c648e38b823054c26ef33f
出典データセット
uspto-grants-2014_02
特許番号
US08658636B2

関連ノート

読み込み中…