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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1392674Generated: October 26, 2026

Ethyl Acetate → 4-[6-(2,6-Diethyl-phenyl)-3-(2,2-dimethyl-morpholin-4-ylmethyl)-2-methyl-pyridin-4-yloxy]-2-hydroxy-benzamide

https://huagongshe.com/reaction/1392674

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl AcetateHCID 8857—
ReactantPotassium CarbonateHCID 11430—
Reactant2,4-DihydroxybenzamideHCID 76601—
Reactant4-[4-Chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholineHCID 59678212—
CatalystCopperHCID 23978—
SolventWaterHCID 962—
SolventN-methyl-2-pyrrolidoneHCID 13387—
Product4-[6-(2,6-Diethyl-phenyl)-3-(2,2-dimethyl-morpholin-4-ylmethyl)-2-methyl-pyridin-4-yloxy]-2-hydroxy-benzamideHCID 59678200—

Reaction Conditions

Temperature150 °C

Reaction Steps

A mixture of 4-[4-chloro-6-(2,6-diethyl-phenyl)-2-methyl-pyridin-3-ylmethyl]-2,2-dimethyl-morpholine (30 mg, 0.08 mmol), 2,4-dihydroxy-benzamide (24 mg, 0.16 mmol), copper powder (10 mg) and K2CO3 (22 mg, 0.16 mmol) in 1-methyl-2-pyrrolidinone (1 mL) is heated at 150° C. overnight. After cooling, EtOAc (10 mL) and water (10 mL) are added to the mixture. The organic layer is separated, washed with brine (3×), dried (Na2SO4) and concentrated. The crude is purified by PTLC (1:1 Hexane/EtOAc) to give to give the title compound. 1H NMR (CDCl3) 12.41 (s, 1H), 7.35 (d, 2H), 7.23 (m, 1H), 7.10 (m, 2H), 6.63 (s, 1H), 6.51 (m, 2H), 5.85 (br, 2H), 3.72 (m, 2H), 3.56 (s, 2H), 2.74 (s, 3H), 2.41-2.30 (m, 6H), 1.20 (s, 6H), 1.76 (m, 2H), 1.01 (t, 6H).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07342115B2
Source datasetuspto-grants-2008_03
ORD IDord-eca786cb8079415dbb54b6a3d0fcdd7b
Source noteuspto-grants-2008_03