反应详情

A solution of 2,4-dihydroxy-3-propylacetophenone (1.008 grams) in dry methanol (10 mL) was treated with hydroxylamine hydrochloride (1.803 grams) and anhydrous sodium acetate (2.127 grams). The mixture was refluxed 4 hours. HPLC analysis indicated the complete disappearance of starting material. The reaction was partitioned between isopropyl acetate and pH 7 buffer. The organic was dried over magnesium sulfate, filtered and evaporated to a solid. Acetic anhydride (11 mL) was added and the solution stirred at ambient temperature for 14 hours. The solvent was removed in vacuo and the residue partitioned between isopropyl acetate and pH 7 buffer. The organic was dried over magnesium sulfate, filtered and concentrated to a residue. Pyridine (12 mL) was added and the solution refluxed for 3 hours. The solvent was removed in vacuo and the residue partitioned between isopropyl acetate and 0.1 N HCl. The organic was washed with 0.1 N HCl and dried over magnesium sulfate. The organic was filtered and concentrated to a residue which was chromatographed over silica gel to afford the title compound.

1. temperatureThe mixture was refluxed 4 hours
2. customThe reaction was partitioned between isopropyl acetate and pH 7 buffer
3. dry with materialThe organic was dried over magnesium sulfate
4. filtrationfiltered
5. customevaporated to a solid
6. additionAcetic anhydride (11 mL) was added
7. customThe solvent was removed in vacuo
8. customthe residue partitioned between isopropyl acetate and pH 7 buffer
9. dry with materialThe organic was dried over magnesium sulfate
10. filtrationfiltered
11. concentrationconcentrated to a residue
12. additionPyridine (12 mL) was added
13. temperaturethe solution refluxed for 3 hours
14. customThe solvent was removed in vacuo
15. customthe residue partitioned between isopropyl acetate and 0.1 N HCl
16. washThe organic was washed with 0.1 N HCl
17. dry with materialdried over magnesium sulfate
18. filtrationThe organic was filtered
19. concentrationconcentrated to a residue which
20. customwas chromatographed over silica gel