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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1747843Generated: November 1, 2026

Ethyl Acetate → 2-Amino-5-methylpyridine-3-carbonitrile

https://huagongshe.com/reaction/1747843

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantSodium HydroxideHCID 14798—
Reactant2-Amino-3-bromo-5-methylpyridineHCID 519380—
ReactantHCID 178418546HCID 178418546—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product2-Amino-5-methylpyridine-3-carbonitrileHCID 1307084213.4%

Reaction Conditions

Temperature180 °C

Reaction Steps

To a solution of 2-amino-3-bromo-5-methylpyridine (3.74 g) in DMF (30 mL) was added copper(I) cyanide (4.48 g), and the mixture was stirred under microwave irradiation at 180° C. for 30 min. To the reaction mixture were added ethyl acetate and water, 1N aqueous sodium hydroxide solution (50 mL) was added and the mixture was stirred. Insoluble material was filtered off through celite. The aqueous layer and organic layer were separated, and the aqueous layer was extracted with ethyl acetate. The extract was collected, washed with saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (357 mg) as a colorless solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09150591B2
Source datasetuspto-grants-2015_10
ORD IDord-c03dfef742004948b5a10d48afe7a056
Source noteuspto-grants-2015_10