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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 498087Generated: October 30, 2026

Water → 4-[N-(tert-butyl)-N-hydroxyamino]-N-(8-hydroxyquinolin-5-yl)-benzamide

https://huagongshe.com/reaction/498087

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantAmmonium ChlorideHCID 25517—
ReactantTetrabutylammonium FluorideHCID 2724141—
Reactant4-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-N-(8-hydroxyquinolin-5-yl)-benzamideHCID 22320718—
SolventTetrahydrofuranHCID 8028—
SolventEthyl AcetateHCID 8857—
Product4-[N-(tert-butyl)-N-hydroxyamino]-N-(8-hydroxyquinolin-5-yl)-benzamideHCID 1015494170.3%

Reaction Steps

To a solution of 0.04 g (0.085 mmol) of compound 9 in THF (1 mL) was added 0.43 mL (0.43 mmol) of 1 M solution of tetrabutylammonium fluoride in THF at room temperature, and the solution was stirred for 1 hour. After completion of the reaction, 2 mL of water was added to quench the reaction. Ethyl acetate and sat'd NH4Cl solution were added to the mixture. The organic layer was separated, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=10:1) to give 0.021 g of compound 10 in 70% yield.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06949654B2
Source datasetuspto-grants-2005_09
ORD IDord-b56c13ee9d884a7aa4b70111b35216e5
Source noteuspto-grants-2005_09