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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1922260Generated: November 2, 2026

Cesium carbonate → 4-(4-amino-3-methylphenoxy)-N-methylpyridine-2-carboxamide

https://huagongshe.com/reaction/1922260

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
Reactant4-Amino-m-cresolHCID 17819—
Reactant4-Chloro-N-methylpicolinamideHCID 1476814—
SolventWaterHCID 962—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product4-(4-amino-3-methylphenoxy)-N-methylpyridine-2-carboxamideHCID 23137246—

Reaction Conditions

Temperature75 °C

Reaction Steps

To the solution of 4-amino-m-cresol (125 mg, 1.01 mmol, 1.0 eq) in 1 mL of NMP was added 4-chloro-N-methylpicolinamide (189 mg, 1.11 mmol, 1.1 eq) and cesium carbonate (658 mg, 2.02 mmol, 2.0 eq) at room temperature. The reaction mixture was stirred at 75° C. for 12 hours, thereafter the mixture was diluted with water (ca. 50 mL) and aqueous layer extracted with ethyl acetate (ca. 50 mL×3). Combined organic layers were dried over sodium sulfate, filtered and condensed under reduced pressure to give sufficiently pure crude product which was carried to next step without further purification. LC/MS (m/z) [258.1] (MH+).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08173689B2
Source datasetuspto-grants-2012_05
ORD IDord-a591cda3773f4bd2ad26d276ff8c975e
Source noteuspto-grants-2012_05