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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1795129Generated: October 30, 2026

Allyl chloride → 1-(6-Chloropyridin-3-yl)pent-4-ene-1,2,2-tricarbonitrile

https://huagongshe.com/reaction/1795129

Reaction equation

Participants

RoleNameHCIDCharge
ReactantAllyl chlorideHCID 7850—
ReactantTrimethylsilyl cyanideHCID 82115—
ReactantHCID 22185757HCID 22185757—
CatalystFerrocene-1,1'-bis-(diphenylphosphine)HCID 635956—
SolventTetrahydrofuranHCID 8028—
Product1-(6-Chloropyridin-3-yl)pent-4-ene-1,2,2-tricarbonitrileHCID 2218575270.9%

Reaction Conditions

Temperature75 °C

Reaction Steps

To tetrahydrofuran (13 ml) were added ((6-Chloro-3-pyridyl)methylidene)malononitrile (0.50 g), tris(dibenzylideneacetone)dipalladium chloroform complex (70 mg) and 1,1′-bis(diphenylphosphino)ferrocene (0.15 g) under nitrogen atmosphere, and then allyl chloride (0.41 g) and trimethylsilylcyanide (0.53 g) were added thereto. The solution was stirred at 75° C. for a day. Then the reaction mixture was filtered through silica gel, and concentrated. The residue was subjected to silica gel column chromatography to give 0.48 g of 1-(6-Chloro-3-pyridyl)-1,2,2-tricyano-4-pentene represented by the following formula (hereinafter referred to as the present invention compound (2)).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07026340B2
Source datasetuspto-grants-2006_04
ORD IDord-97e505ba97ca43308f83271af7c9fdd4
Source noteuspto-grants-2006_04