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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1427015Generated: October 26, 2026

Water → 4-((6-Ethoxy-1H-indol-5-yl)oxy)pyridin-2-amine

https://huagongshe.com/reaction/1427015

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantEthyl AcetateHCID 8857—
ReactantSodium HydroxideHCID 14798—
ReactantN-(4-((6-Ethoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamideHCID 86730318—
SolventMethanolHCID 887—
Product4-((6-Ethoxy-1H-indol-5-yl)oxy)pyridin-2-amineHCID 8673031986%

Reaction Conditions

Temperature75 °C

Reaction Steps

N-(4-((6-ethoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 15-5 (7.16 g, 23.0 mmol) was dissolved in methanol (50 mL), a 2 M sodium hydroxide solution (50 mL) was added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 75° C. for 2.5 hours. The reaction mixture was cooled to room temperature and then water and ethyl acetate were added for partition. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate, then the resultant was filtered and concentrated under vacuum. A liquid mixture of diethyl ether and ethyl acetate was added to the residue, and the mixture was collected by filteration and washed to obtain the title compound (5.35 g, 86%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08933099B2
Source datasetuspto-grants-2015_01
ORD IDord-f2bbdf2c1936413ca68f54c711e569b5
Source noteuspto-grants-2015_01