Potassium Hydroxide → 5-Bromo-7-chloroindoline

HRID 1060622Notes

Reaction equation

HRID 1060622 reaction equation
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([Br:14])=[CH:10][C:11]=2[Cl:13])[CH2:6][CH2:5]1)(=O)C.[OH-].[K+]>C(O)C.O>[Br:14][C:9]1[CH:8]=[C:7]2[C:12](=[C:11]([Cl:13])[CH:10]=1)[NH:4][CH2:5][CH2:6]2

Participants

5

Reactant 2

HCID 14797Potassium HydroxideHCID 186292691-(5-Bromo-7-chloro-2,3-dihydro-1H-indol-1-yl)ethan-1-one

Product 1

HCID 167891645-Bromo-7-chloroindolineYield 87.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Part B: 1-acetyl-5-bromo-7-chloroindoline (1.17 g) was dissolved in a mixture of ethanol (15 mL) and water (8 mL) containing KOH (0.5 g) and heated to reflux for 2 h. The reaction was partitioned between EtOAc (100 mL) and water (20 mL). The organic extract was washed with brine (20 mL), dried and stripped in vacuo to give 5-bromo-7-chloroindoline (0.87 g).

Workup

  1. temperatureheated
  2. temperatureto reflux for 2 h
  3. customThe reaction was partitioned between EtOAc (100 mL) and water (20 mL)
  4. extractionThe organic extract
  5. washwas washed with brine (20 mL)
  6. customdried

Sources & evidence

ORD record
ord-8ee73df8cb29452c817807b2032d3d5d
Source dataset
uspto-grants-2003_02
Patent number
US06525056B2

Reaction notes

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