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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2366085Generated: October 31, 2026

Water → N-acetyl-4-(pyrid-2-ylmethoxy)aniline

https://huagongshe.com/reaction/2366085

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantAcetaminophenHCID 1983—
ReactantCesium carbonateHCID 10796—
ReactantPicolyl chloride hydrochlorideHCID 23392—
SolventDimethylformamideHCID 6228—
ProductN-acetyl-4-(pyrid-2-ylmethoxy)anilineHCID 1909833596.6%

Reaction Conditions

Temperature70 °C

Reaction Steps

A mixture of 4-acetamidophenol (Sigma-Aldrich; 73.6 g), 2-chloromethylpyridine hydrochloride (80 g) and cesium carbonate (320 g) in DMF (1 L) was stirred at 70° C. for 2 days. The mixture was cooled, poured into water (2 L) and extracted with EtOAC (×6). The organic layers were washed with brine, dried (MgSO4) and filtered to give a tan solid (114 g) which was used as such in the next step.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08697730B2
Source datasetuspto-grants-2014_04
ORD IDord-65989a8012bb476e82189ab670ca11e5
Source noteuspto-grants-2014_04