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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1266285Generated: October 25, 2026

Toluene → 6-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile

https://huagongshe.com/reaction/1266285

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTolueneHCID 1140—
ReactantTrifluoroacetic acidHCID 6422—
Reactant4-(3-Bromo-phenylamino)-6-(4-methoxy-benzylamino)-[1,7]naphthyridine-3-carbonitrileHCID 12969105—
SolventDichloromethaneHCID 6344—
Product6-Amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrileHCID 979800684.6%

Reaction Steps

To 400 mg of 4-(3-bromo-phenylamino)-6-(4-methoxy-benzylamino)-[1,7]naphthyridine-3-carbonitrile in 10 mL of methylene chloride was added 10 mL of trifluoroacetic acid. After stirring under an inert atmosphere for 20 hours, 10 mL of toluene was added and the solvents were stripped on a rotary evaporator. The product was purified by flash chromatography with a gradient of 0-5% methanol/chloroform to give 250 mg of 6-amino-4-(3-bromo-phenylamino)-[1,7]naphthyridine-3-carbonitrile as an off-white solid: melting point 185-190° C. (decomposed); mass spectrum (m/e): M+H 340.0, 342.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS06548496B2
Source datasetuspto-grants-2003_04
ORD IDord-b112f7fdb3244175b4bd717f07911945
Source noteuspto-grants-2003_04