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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1921832Generated: October 31, 2026

Morpholine → 4-(6-Nitropyridin-3-yl)morpholine

https://huagongshe.com/reaction/1921832

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMorpholineHCID 8083—
ReactantPotassium CarbonateHCID 11430—
Reactant5-Bromo-2-nitropyridineHCID 817620—
CatalystTetrabutylammonium IodideHCID 67553—
SolventDimethyl SulfoxideHCID 679—
SolventEthyl AcetateHCID 8857—
Product4-(6-Nitropyridin-3-yl)morpholineHCID 292797346.2%

Reaction Conditions

Temperature80 °C

Reaction Steps

A mixture of 5-bromo-2-nitro-pyridine (5 g, 24.75 mmol), tetrabutyl ammonium iodide (0.46 g, 1.24 mmol), K2CO3 (3.76 g, 27.22 mmol) and morpholine (2.34 g, 27.22 mmol) in DMSO (50 mL) is stirred at 80° C. in a stem tube for 20 hours. The reaction mixture is diluted with ethyl acetate and filtered. The organic solution is washed with water, dried over MgSO4 and concentrated in vacuo. The residue is triturated with dichloromethane and hexane to afford the title compound as a solid (2.39 g, 46%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08173656B2
Source datasetuspto-grants-2012_05
ORD IDord-8a953f44ab9a43dfa427e1c31f197fb8
Source noteuspto-grants-2012_05