Sulfuric Acid → 5-Bromo-7-ethylindoline-2,3-dione

HRID 2249528

反応式

HRID 2249528 の反応式
S(=O)(=O)(O)[OH:2].[Br:6][C:7]1[CH:12]=[CH:11][C:10]([NH:13][C:14](=[O:18])[CH:15]=NO)=[C:9]([CH2:19][CH3:20])[CH:8]=1>O>[Br:6][C:7]1[CH:12]=[C:11]2[C:10](=[C:9]([CH2:19][CH3:20])[CH:8]=1)[NH:13][C:14](=[O:18])[C:15]2=[O:2]

参加物

4

反応物 2

HCID 1118Sulfuric AcidHCID 86041545N-(4-Bromo-2-ethyl-phenyl)-2-hydroxyimino-acetamide

生成物 1

HCID 80338135-Bromo-7-ethylindoline-2,3-dione収率 74%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a solution of sulfuric acid (100 mL) and water (10 mL) at 80° C. (oil bath) was added N-(4-bromo-2-ethyl-phenyl)-2-hydroximino-acetoamide (61.0 g, 225 mmol) in small portions over 20 minutes. The reaction mixture was heated at 80° C. (oil bath) for 15 minutes. After cooling to room temperature, ice-water (500 mL) was added and the mixture was extracted with ethyl acetate. Extracts were washed with saturated sodium bicarbonate solution, dried over magnesium sulfate, and concentrated under reduced pressure to give the title compound (42.3 g, 74% yield). 1H NMR (DMSO-d6) δ 8.87 (s, 1H), 7.75 (d, 1H), 7.71 (d, 1H), 2.75 (q, 2H), 1.44 (t, 3H).

後処理

  1. temperatureAfter cooling to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. washExtracts were washed with saturated sodium bicarbonate solution
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-38f1b47e28114101bfcce833626d4d29
出典データセット
uspto-grants-2008_01
特許番号
US07314886B2

関連ノート

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