Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1437463Generated: October 31, 2026

Toluene → 3-Nitro-6-phenylpyridin-2-amine

https://huagongshe.com/reaction/1437463

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantSodium CarbonateHCID 10340—
ReactantPhenyl dihydrogen orthoborateHCID 78412—
Reactant6-Chloro-3-nitropyridin-2-ylamineHCID 2724035—
CatalystHCID 178418397HCID 178418397—
SolventWaterHCID 962—
SolventTetrahydrofuranHCID 8028—
SolventTetrahydrofuran ethyl acetateHCID 21939870—
Product3-Nitro-6-phenylpyridin-2-amineHCID 1056061953%

Reaction Conditions

Temperature90 °C

Reaction Steps

Under an argon stream, a mixture of 6-chloro-3-nitro-2-pyridine amine (2.0 g), phenylboric acid (2.1 g), tetrakis(triphenylphosphine)palladium(0) (1.3 g), 2 M sodium carbonate (35 ml), toluene (40 ml) and tetrahydrofuran (20 ml) was stirred at 90° C. for 12 hours. The mixture was distributed into ethyl acetate-tetrahydrofuran (3:1, v/v) and water. The organic layer was washed with water and dried over MgSO4. The solvent was distilled off under reduced pressure and the resulting crystals were collected by filtration to obtain 3-nitro-6-phenyl-2-pyridine amine (1.3 g, 53%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07622479B2
Source datasetuspto-grants-2009_11
ORD IDord-6fa2f26bc55a48d4927428721dc2d765
Source noteuspto-grants-2009_11