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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1091546Generated: October 27, 2026

Dimethylformamide → 5-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-one

https://huagongshe.com/reaction/1091546

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant3-(2-Ethoxyphenyl)-3-hydroxy-5-iodoindol-2-oneHCID 57466442—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
Product5-Cyano-3-(2-ethoxyphenyl)-3-hydroxy-indol-2-oneHCID 66593041—

Reaction Steps

37.2 g (94 mmol) of the product 1a and 11.1 g (94 mmol) of zinc cyanide in 300 ml of DMF were heated to 95° C. Then 1.6 g (1.38 mmol) of tetrakis(triphenylphosphine)palladium(0) were added in portions every 10 minutes. After 45 minutes, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The organic phase was washed with saturated NaCl solution, dried and concentrated in vacuo. The residue obtained in this way crystallizes from a little ethyl acetate. 24 g of the product were obtained.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08129389B2
Source datasetuspto-grants-2012_03
ORD IDord-3cc875744e834416adb627209d00f9f1
Source noteuspto-grants-2012_03