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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2202913Generated: October 28, 2026

Ammonia → 4-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-one

https://huagongshe.com/reaction/2202913

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAmmoniaHCID 222—
ReactantN,N'-DimethylethylenediamineHCID 8070—
ReactantPotassium CarbonateHCID 11430—
Reactant5-bromo-N-methyl-2-nitroanilineHCID 10609530—
Reactant4-[(4-Chlorophenyl)methoxy]pyridin-2(1H)-oneHCID 57497864—
CatalystCopper iodideHCID 83717—
SolventDimethyl SulfoxideHCID 679—
Product4-(4-Chlorobenzyloxy)-1-(3-(methylamino)-4-nitrophenyl)pyridin-2(1h)-oneHCID 8969116873.3%

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of 4-((4-chlorobenzyl)oxy)pyridin-2(1H)-one (10 g), 5-bromo-N-methyl-2-nitroaniline (9.80 g), N,N′-dimethylethylenediamine (4.76 ml), copper iodide (8.08 g), potassium carbonate (17.59 g) and DMSO (200 ml) was heated at 150° C. for 2 h. The mixture was poured into 28% NH3 solution. The resulting precipitate was collected and washed with IPA. The solid was dissolved in DMSO (100 ml) at 80° C., and allowed to cool to room temperature to give a precipitate. After filtration, the precipitate was washed with IPA and dried to give the title compound (12 g) as a yellow solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09365540B2
Source datasetuspto-grants-2016_06
ORD IDord-982af0a26e344a98bac3ee14ed7821f9
Source noteuspto-grants-2016_06