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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 530800Generated: October 27, 2026

Dimethylformamide → 5-Amino-6-methylpicolinonitrile

https://huagongshe.com/reaction/530800

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethylformamideHCID 6228—
Reactant6-Bromo-2-methylpyridin-3-amineHCID 14418045—
CatalystZinc cyanide (Zn(CN)2)HCID 11186—
CatalystHCID 178418397HCID 178418397—
SolventMethanolHCID 887—
SolventWaterHCID 962—
Product5-Amino-6-methylpicolinonitrileHCID 55252984—

Reaction Conditions

Temperature110 °C

Reaction Steps

To a solution of 6-bromo-2-methylpyridin-3-amine (compound 1, 500 mg, 2.69 mmol) in DMF (10 mL) was added Zn(CN)2 (943 mg, 8.06 mmol) and Pd(PPh3)4 (288 mg, 0.3 mmol) at room temperature. The reaction was stirred at 110° C. in microwave reactor for 1 h. After it was cooled to room temperature, the mixture was filtered and purified by reverse phase chromatography (X bridge Prep C18OBD, 40-60% MeOH in water with 10 mmol NH4HCO3 modifier) to afford the compound as an oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09353104B2
Source datasetuspto-grants-2016_05
ORD IDord-3d0369d5e7464d0e9e0babe420854add
Source noteuspto-grants-2016_05