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

HRID 530733Notes

Reaction equation

HRID 530733 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 recrystallized 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 recrystallized from EtOH

Sources & evidence

ORD record
ord-f39001bbf42543a49e0615cba31cff41
Source dataset
uspto-grants-2016_05
Patent number
US09353100B2

Reaction notes

Loading…