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

HRID 2249528Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2249528
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]

Komponenten

4

Edukt 2

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

Produkt 1

HCID 80338135-Bromo-7-ethylindoline-2,3-dioneAusbeute 74 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-38f1b47e28114101bfcce833626d4d29
Quelldatensatz
uspto-grants-2008_01
Patentnummer
US07314886B2

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