Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 279014Generated: October 29, 2026

Diethyl Ether → 5-Bromo-2-hydroxy-6-(piperidine-1-yl)-benzo[de]isoquinoline-1,3-dione

https://huagongshe.com/reaction/279014

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDiethyl EtherHCID 3283—
Reactant2-Benzyloxy-5-bromo-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 22623913—
ReactantHCID 178525683HCID 178525683—
SolventTrifluoroacetic acidHCID 6422—
Product5-Bromo-2-hydroxy-6-(piperidine-1-yl)-benzo[de]isoquinoline-1,3-dioneHCID 2262403327.6%

Reaction Conditions

Temperature0 °C

Reaction Steps

To a solution of 2-benzyloxy-5-bromo-6-(piperidin-1-yl)-benzo[de]isoquinoline-1,3-dione (0.27 g, 0.58 mmol, from Example T1-A) in TFA (5 mL) at 0° C. was added a 1.0 M solution of boron tris(trifluoroacetate) in TFA (3 mL). The reaction was stirred at 0° C. for 2 hours. Ethyl ether was added forming a precipitate which was collected by filtration. The solid was taken up in chloroform, the organic layer washed with water, dried, filtered, and evaporated under reduced pressure to give 0.060 g of the title compound as the TFA salt, mp >250° C.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06362181B1
Source datasetuspto-grants-2002_03
ORD IDord-a1e8b716a6484ca9911a748dc98b172f
Source noteuspto-grants-2002_03