Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2406751Generated: October 26, 2026

Morpholine → 2-Methoxy-3-morpholino-5-nitropyridine

https://huagongshe.com/reaction/2406751

Reaction equation

Participants

RoleNameHCIDCharge
ReactantMorpholineHCID 8083—
ReactantCesium carbonateHCID 10796—
Reactant1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 636044—
Reactant3-Bromo-2-methoxy-5-nitropyridineHCID 21584451—
CatalystBis(dibenzylideneacetone)palladiumHCID 9811564—
SolventWaterHCID 962—
Solvent1,4-DioxaneHCID 31275—
Product2-Methoxy-3-morpholino-5-nitropyridineHCID 68027925—

Reaction Conditions

Temperature100 °C

Reaction Steps

Morpholine (54 μl), cesium carbonate (336 mg), Pd2(dba)3 (57 mg), and Xantphos (72 mg) were added to a 1,4-dioxane (3 ml) solution containing 3-bromo-2-methoxy-5-nitropyridine (96 mg) in a nitrogen atmosphere, followed by stirring at 100° C. for 10 hours. The reaction solution was adjusted to room temperature, and water was added, followed by extraction with ethyl acetate. The resultant was washed with saturated saline and dried over anhydrous sodium sulfate, and the solvent was distilled away under reduced pressure. The obtained residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1 to 2:1), and a yellow solid of 2-methoxy-3-morpholino-5-nitropyridine (54 mg) was thus obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08809371B2
Source datasetuspto-grants-2014_08
ORD IDord-74b750d8a68a45c69747dca36a6b76c5
Source noteuspto-grants-2014_08