Boron trifluoride etherate → 7-chloro-6-methoxy-1H-indole-2,3-dione

HRID 1675433Notes

Reaction equation

HRID 1675433 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[CH:4][C:3]=1[NH:10][C:11](=[O:15])[CH:12]=NO.B(F)(F)F.CC[O:22]CC>>[Cl:1][C:2]1[C:7]([O:8][CH3:9])=[CH:6][CH:5]=[C:4]2[C:3]=1[NH:10][C:11](=[O:15])[C:12]2=[O:22]

Participants

3

Reactant 2

HCID 8000Boron trifluoride etherateHCID 86633207N-(2-chloro-3-methoxyphenyl)-2-hydroxyimino-acetamide

Product 1

HCID 666505277-chloro-6-methoxy-1H-indole-2,3-dioneYield 63%

Conditions

Temperature
90 °C

Procedure

Compound 102d (10.46 g, 45.74 mmol) was added portionwise to BF3.Et2O at 40° C. The mixture was then heated at 90° C. for 3 hrs. After cooling down to room temperature, the reaction mixture was poured into crushed ice and extracted with EtOAc. Organics were dried over Na2SO4, filtered, concentrated under reduced pressure, and purified by chromatography on silica gel (petroleum ether/EtOAc). The compound obtained was recrystallised from EtOH to yield compound 103d as a brown solid in 63% yield.

Workup

  1. temperatureAfter cooling down to room temperature
  2. additionthe reaction mixture was poured
  3. custominto crushed ice
  4. extractionextracted with EtOAc
  5. dry with materialOrganics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. custompurified by chromatography on silica gel (petroleum ether/EtOAc)
  9. customThe compound obtained
  10. customwas recrystallised from EtOH

Sources & evidence

ORD record
ord-dc9b409d22c641f5acdd5499ce61f45c
Source dataset
uspto-grants-2011_08
Patent number
US08003659B2

Reaction notes

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