反应详情

温度

0 °C

3-Amino-6-chloro-2-(2-furanyl)-4-methylpyridine (400 mg) was dissolved in acetone (10 mL) and cooled in an ice bath to 0° C. A solution prepared of potassium permanganate (909 mg) in water (15 mL) was added drop wise to this solution. After complete addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 hours. The mixture was cooled again to 0° C. and a second portion of potassium permanganate (600 mg) in water (10 mL) was added and the cool bath removed. After stirring for 2 hours, the reaction mixture was filtered through a pad of celite, the filter cake was washed carefully with water, methanol and ethyl acetate and concentrated to approx. 10 mL on a rotary evaporator. 2N Sodium hydroxide solution was added to adjust the pH-value to −12 and the aqueous layer was washed 2× with MTB-ether. The aqueous layer was then adjusted to pH ˜2 by addition of 6N hydrochloric acid and extracted 3× with MTB-ether. The combined organic layer was washed with brine, dried over MgSO4 and concentrated in vacuum to afford 262 mg of the title compound of the formula

1. additionwas added drop wise to this solution
2. additionAfter complete addition
3. temperatureto warm to room temperature
4. temperatureThe mixture was cooled again to 0° C.
5. customthe cool bath removed
6. stirringAfter stirring for 2 hours
7. filtrationthe reaction mixture was filtered through a pad of celite
8. washthe filter cake was washed carefully with water, methanol and ethyl acetate
9. concentrationconcentrated to approx. 10 mL on a rotary evaporator
10. addition2N Sodium hydroxide solution was added
11. washthe aqueous layer was washed 2× with MTB-ether
12. additionThe aqueous layer was then adjusted to pH ˜2 by addition of 6N hydrochloric acid
13. extractionextracted 3× with MTB-ether
14. washThe combined organic layer was washed with brine
15. dry with materialdried over MgSO4
16. concentrationconcentrated in vacuum