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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 420071Generated: October 29, 2026

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

https://huagongshe.com/reaction/420071

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron trifluoride etherateHCID 8000—
ReactantN-(2-chloro-3-methoxyphenyl)-2-hydroxyimino-acetamideHCID 86633207—
Product7-chloro-6-methoxy-1H-indole-2,3-dioneHCID 6665052763%

Reaction Conditions

Temperature90 °C

Reaction Steps

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.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08093379B2
Source datasetuspto-grants-2012_01
ORD IDord-bbb350076b8b4b049e93ef0c353222ed
Source noteuspto-grants-2012_01