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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 713820Generated: October 31, 2026

2-Chloroethanol → 2-(1,1-Dicyanopropen-2-yl)-6-{[2-(2-hydroxy-ethoxy)-ethyl]methylamino}naphthalene

https://huagongshe.com/reaction/713820

Reaction equation

Participants

RoleNameHCIDCharge
Reactant2-ChloroethanolHCID 34—
Reactant(1-(6-((2-Hydroxyethyl)(methyl)amino)-2-naphthyl)ethylidene)malononitrileHCID 18761122—
SolventAcetonitrileHCID 6342—
Product2-(1,1-Dicyanopropen-2-yl)-6-{[2-(2-hydroxy-ethoxy)-ethyl]methylamino}naphthaleneHCID 11850936760%

Reaction Conditions

Temperature80 °C

Reaction Steps

0.40 g (1.4 mmol) of the fourth compound 4 is obtained to be dissolved in 8 mL of anhydrous acetonitrile. 0.35 g (4.3 mmol) of 2-chloro-ethanol is added to be heated with stirring at 80° C. for 17 hrs. After cooling, extraction is processed with dichloromethane. After being dried with anhydrous sodium sulfate, an organic phase is concentrated under reduced pressure to be separated and purified by liquid chromatography (SiO2, CHCl3:EtOAc=1:1). Thus, a product, 2-(1,1-dicyanopropen-2-yl)-6-{[2-(2-hydroxy-ethoxy)-ethyl]methylamino}naphthalene 5 (hereinafter referred to as fifth compound 5), is obtained, which has a weight of 0.29 g and a yield of 60.0%.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09186423B1
Source datasetuspto-grants-2015_11
ORD IDord-5b82f0fe56ec4fe897ea5ebfaf8a2be3
Source noteuspto-grants-2015_11