Water → HCID 66936456, compound

Hydroxy-acetic acid methyl ester (3.96 g, 47.0 mmol) was dissolved in 50 ml of anhydrous tetrahydrofuran under nitrogen atmosphere, and sodium hydride (2.01 g, 53.2 mmol) was added thereto at room temperature. After stirring for 30 minutes, 2-chloro-5-methyl-3-nitro-pyridine (5.39 g, 31.3 mmol) dissolved in 15 ml of anhydrous tetrahydrofuran was added dropwise at room temperature, and the reaction mixture was stirred at room temperature for 18 hours. After completion of the reaction by adding water, the mixture was extracted with ethyl acetate, and the combined organic layer was washed with water and saturated saline solution, dried over anhydrous sodium sulfate (Na2SO4), filtered and evaporated under reduced pressure. The resulting solid was recrystallized from dichloromethane and ether to obtain (5-methyl-3-nitro-pyridin-2-yloxy)-acetic acid methyl ester as yellow solid (5.47 g, 77%).

1. customat room temperature
2. additionwas added dropwise at room temperature
3. stirringthe reaction mixture was stirred at room temperature for 18 hours
4. customAfter completion of the reaction
5. extractionthe mixture was extracted with ethyl acetate
6. washthe combined organic layer was washed with water and saturated saline solution
7. dry with materialdried over anhydrous sodium sulfate (Na2SO4)
8. filtrationfiltered
9. customevaporated under reduced pressure
10. customThe resulting solid was recrystallized from dichloromethane and ether

ORD record

ord-a1f26dcc673c4418a5277c2fa51212a3

Source dataset

uspto-grants-2013_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08394792B2