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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2266931Generated: October 31, 2026

2-Methyl-1-naphthylamine → HCID 58114881, compound

https://huagongshe.com/reaction/2266931

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-Methyl-1-naphthylamineHCID 16733—
Reactant2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 2734217—
ReactantSodium t-butoxideHCID 23676156—
ReactantHCID 58114889HCID 58114889—
Catalyst(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumHCID 6505921—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductHCID 58114881HCID 58114881—

Reaction Conditions

Temperature100 °C

Reaction Steps

A mixture of 8-bromo-2-(1-naphthyl)quinoline (3.25 g, 9.7 mmol), 2-methyl-1-naphthalenamine (1.76 g, 11.2 mmol), Pd(dba)2 (0.12 g, 0.2 mmol), L=(N-[2′-(dicyclohexylphosphino)[1,1′-biphenyl]-2-yl]-N,N-dimethylamine (0.15 g, 0.4 mmol), NaOtBu (1.15 g, 12 mmol) and toluene (20 mL) is stirred for 8 h under an argon atmosphere at 100° C. in oil bath. The mixture is then poured into water and extracted with benzene (3×40 mL). The combined organic phases are washed with water and brine and then concentrated. The residue is purified by column chromatography (silica gel 40, hexane/toluene 4:1). Yield 3.1 g (78%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07858718B1
Source datasetuspto-grants-2010_12
ORD IDord-ccdbbac95b574b1db30858ebee76c074
Source noteuspto-grants-2010_12