反应详情

5-amino-2-methoxypyridine(3.18 g), chloroacetic anhydride(6.56 g), and triethylamine(7.09 ml) were stirred in benzene(55 ml) for 1 hour while being cooled with ice. The reaction mixture, with water added thereto, was extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum. To the solution of the residue in dimethylformamide(20 ml) was added potassium phthalimide(5.21 g) and then the mixture was refluxed with stirring for 3 hours. After a large amount of water was added thereto, the depositing crystal was collected by filtration. The solution of the crystal in ethanol(120 ml), with hydrazine monohydrate(2.56 ml) was refluxed with stirring for 2 hours and then concentrated under a vacuum. The residue, with water added thereto, was acidified with sodium hydrogencarbonate and then extracted with ethyl acetate. The extract was dried over sodium sulfate anhydride and then concentrated under a vacuum. The solution of the residue in tetrahydrofuran(40 ml) was dropped into the suspension of lithium aluminium hydride(2.63 g) in tetrahydrofuran(40 ml) while being cooled with ice and the mixture was stirred at room temperature for 2 hours. A small amount of water was added thereto and the resulting deposit was filtrated out. The filtrate was concentrated under a vacuum, thereby yielding 2.12 g of the aimed compound.

1. temperaturewhile being cooled with ice
2. extractionwas extracted with ethyl acetate
3. dry with materialThe extract was dried over sodium sulfate anhydride
4. concentrationconcentrated under a vacuum
5. additionTo the solution of the residue in dimethylformamide(20 ml) was added potassium phthalimide(5.21 g)
6. temperaturethe mixture was refluxed
7. additionAfter a large amount of water was added
8. filtrationthe depositing crystal was collected by filtration
9. temperatureThe solution of the crystal in ethanol(120 ml), with hydrazine monohydrate(2.56 ml) was refluxed
10. stirringwith stirring for 2 hours
11. concentrationconcentrated under a vacuum
12. additionThe residue, with water added
13. extractionextracted with ethyl acetate
14. dry with materialThe extract was dried over sodium sulfate anhydride
15. concentrationconcentrated under a vacuum
16. additionThe solution of the residue in tetrahydrofuran(40 ml) was dropped into the suspension of lithium aluminium hydride(2.63 g) in tetrahydrofuran(40 ml)
17. temperaturewhile being cooled with ice
18. stirringthe mixture was stirred at room temperature for 2 hours
19. additionA small amount of water was added
20. filtrationthe resulting deposit was filtrated out
21. concentrationThe filtrate was concentrated under a vacuum