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

HRID 268649Notes

Reaction equation

HRID 268649 reaction equation
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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-ea8eaf21ef8e48909001cf7deaafa623
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Reaction notes

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