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

HRID 880782Notes

Reaction equation

HRID 880782 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 245d (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 246d as a brown solid in 63% yield. 1H NMR (DMSO-d6, 400 MHz) δ (ppm) 3.96 (s, 3H), 6.79 (d, J=9.10 Hz, 1H), 7.52 (d, J=9.10 Hz, 1H), 11.40 (s, 1H).

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-cdf7f8855fb145359b5f2f40e029fa85
Source dataset
uspto-grants-2015_03
Patent number
US08993595B2

Reaction notes

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