3-Hydroxypicolinic Acid → 3-hydroxy-2-(N,N-dimethylaminooxycarbonyl)pyridine

7.0 Grams of 3-hydroxypicolinic acid was dissolved in 10 ml of N,N-dimethylformamide, and the resulting solution was cooled to 0° to 5° C. 5.9 Grams of thionyl chloride was then added dropwise to the solution which was then stirred at 0° to 5° C. for further 30 minutes. Thereafter, 30 ml of chloroform was added to the solution which was then stirred at 0° to 5° C. for further 15 minutes. To the resulting mixed solution was added dropwise a dichloromethane solution of N,N-dimethylhydroxylamine prepared from 7.4 g of N,N-dimethylhydroxylamine hydrochloride and 7.6 g of triethylamine. After stirring at 0° to 5° C. for 30 minutes, 7.9 g of pyridine was added, and stirring was continued at 0° to 5° C. for further 1 hour. After stirring at room temperature for 8 hours, the reaction solution was poured into water, and insoluble matters were removed by filtration on celite. The organic layer was washed with water and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the residue obtained was subjected to chromatography to obtain 1.0 g of 3-hydroxy-2-(N,N-dimethylaminooxycarbonyl)pyridine.

1. temperaturethe resulting solution was cooled to 0° to 5° C
2. stirringwas then stirred at 0° to 5° C. for further 15 minutes
3. additionTo the resulting mixed solution
4. stirringAfter stirring at 0° to 5° C. for 30 minutes
5. stirringstirring
6. waitwas continued at 0° to 5° C. for further 1 hour
7. stirringAfter stirring at room temperature for 8 hours
8. customwere removed by filtration on celite
9. washThe organic layer was washed with water
10. dry with materialdried over anhydrous magnesium sulfate
11. customThe solvent was removed under reduced pressure
12. customthe residue obtained

ORDレコード

ord-be722900306f43369bf3d888b78e06c0

出典データセット

uspto-grants-1994_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05300640