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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1366243Generated: October 31, 2026

Dimethyl Sulfoxide → 5-Formylpyridine-2-carbonitrile

https://huagongshe.com/reaction/1366243

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
ReactantTriethylamineHCID 8471—
ReactantOxalyl chlorideHCID 65578—
Reactant2-Cyano-5-hydroxymethylpyridineHCID 12251966—
SolventDichloromethaneHCID 6344—
Product5-Formylpyridine-2-carbonitrileHCID 10986263—

Reaction Conditions

Temperature-78 °C

Reaction Steps

1.04 g (8.2 mmol) oxalylchloride are dissolved in 8 ml dichloromethane. At −78° C., 1.28 g (16.4 mmol) dimethylsulfoxide are added dropwise. The solution is stirred at −78° C. for 20 minutes, then 1 g (7.46 mmol) of the compound of Example 2A, dissolved in 7 ml dichloromethane, is added, and stirring at −78° C. is continued for another 2 hours. 3.4 g (33.6 mmol) triethylamine are then added dropwise, and after warming up to room temperature, the mixture is purified by column chromatography (silica, eluent: cyclohexane to cyclohexane/ethyl acetate 2:1).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07893073B2
Source datasetuspto-grants-2011_02
ORD IDord-a76dba7dd17d4748a902f0e6acfc1707
Source noteuspto-grants-2011_02