3,3-Dibromo-2,3-dihydro-2-oxo-1H-indole-5-carbonitrile → 2-Oxo-2,3-dihydro-1H-indole-5-carbonitrile

HRID 843995Notes

Reaction equation

HRID 843995 reaction equation
Br[C:2]1(Br)[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4][C:3]1=[O:13]>C(O)(=O)C.[Zn]>[O:13]=[C:3]1[CH2:2][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4]1

Participants

4

Reactant 1

HCID 138640893,3-Dibromo-2,3-dihydro-2-oxo-1H-indole-5-carbonitrile

Product 1

HCID 27733462-Oxo-2,3-dihydro-1H-indole-5-carbonitrileYield 36.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 3,3-Dibromo-2-oxo-2,3-dihydro-1H-indole-5-carbonitrile (10.5 grams, 33.3 mmole) and Zn dust (22.0 grams, 338.5 mmole) in acetic acid (250 ml) was stirred at room temperature for 45 minutes. The mixture was filtered through celite and concentrated to dryness. The resulting oil was diluted with 300 ml water and extracted with ethyl acetate. The combined extracts were washed with 1 N sodium hydroxide and brine, dried over MgSO4, filtered, and concentrated to give a white solid (1.9 g). MW 158.

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated to dryness
  3. additionThe resulting oil was diluted with 300 ml water
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with 1 N sodium hydroxide and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-363855d9d1804ac4b5dcda75788b2561
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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